


The Myth of Castiel Novak

by adestielable



Category: Supernatural
Genre: (Present) Explicit Consent, Alternate Universe, Alternate Universe - Pirate, Angel Descendant Castiel, Bottom Castiel, Bottom Castiel/Top Dean Winchester, Coming Untouched, Dean Has Issues, Dean Has PTSD - Post-Traumatic Stress Disorder, Dom Dean, Dom/sub Undertones, Explicit Consent, Explicit Sexual Content, Graphic Descriptions (just to be safe), Happy Ending, Light BDSM, Loss of Virginity, Mildly Graphic Descriptions, Multi, Nipple Play, Other Additional Tags to Be Added, Past Abused Dean Winchester, Past Benny Lafitte/Dean Winchester, Past Child Abuse, Past Rape/Non-con, Pirate Dean, Pirate Sam, Porn With Plot, Post-Traumatic Stress Disorder - PTSD, Protective Dean Winchester, Rape Recovery, Semi-Angel Castiel, Sub Castiel, Top Dean, Twink Castiel, Understanding Castiel
Language: English
Status: In-Progress
Published: 2017-02-04
Updated: 2018-08-29
Packaged: 2018-09-21 23:41:51
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 19
Words: 124,447
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9572075
Author URL: https://archiveofourown.org/users/adestielable/pseuds/adestielable
Summary: Dean "The Righteous Man" Winchester of the Impala 67 was the Pirate King. Fierce, merciless, formidable... You name it. He was everything any pirate could ever hope to be and more. You'd have to be living under a rock to not have heard of him or his crew aboard the biggest ship to sail the seas: the Impala 67.On September 18th, 1692, the governor of the City of Heaven, Michael Novak, faces his biggest fear: Dean Winchester stopped at his docks. Michael's sole goal was to see Dean Winchester and each and every one of his men and woman on his ship's crew hanged.That evening, Dean meets a young man with black hair and striking blue eyes. "Cas," he tells Dean his name. What was Dean to do but offer the gold in his pocket to the kid who looked as if he'd just been fucked in a dirty alley?Cas accepts and 17 gold, a short walk, and a few orgasms later, the two are fast asleep on Dean's bed. For the first time in years, Dean didn't have any of the normal nightmares from his past; and Cas fell asleep feeling protected and safe in the Pirate Kings arms.That night was just the beginning for Dean and Cas. The beginning to something neither wanted to end.





	1. Chapter One

**Author's Note:**

> Hope you enjoy!

Chapter One

_September 18, 1692_

 

Dean “ _The Righteous Man_ ” Winchester of the Impala 67 is a terrifying man... He’s the only pirate to be truly scared of if there ever was one. The crimes he’s been said to have committed are absolutely ruthless and ghastly. The only people to never have heard of him were the ones living six feet under.

That’s why when the Impala 67 docked in the city of Heaven, the people stayed as far away as they could from it and parted to the gutters in the streets when they saw anyone from the pirate’s crew walk down their roads.

Dean and his crew were not affected by this. Other than the occasional ship raiding and murder out in the waters, they were good and honest men and women.

“Oi!” Sam, Dean Winchester’s younger brother, called down from the side of the ship to where Dean was on the docks. “What do you want the swabs to do?”

“Let ‘em rest; for now. They’ve been working their asses off. But get me Benny; we need to start the inventory,” Dean yelled back, shielding his eyes from the afternoon sun.

“Aye aye!” Sam smiled and ran off to go get Benny, the barbecue.

Dean gazed out at the city of Heaven and caught many people sneaking glances at his ship. He couldn’t blame them. It wasn’t every day that you got to see  _the largest ship_ in the world drop anchor at your docks.

As he watched, Dean saw a small boy starting to walk towards the docks, looking up at Dean’s baby with awe. Feeling his brows knit together, he started walking over to the boy. People can say what they want about Dean Winchester of the Impala 67, but he was a decent man.

The young boy, no more than five Dean thought, was getting too close and he didn’t want to see anything happen to the child.

It wasn’t until the child first stepped his foot onto the uneven wood that made up the docks did Dean speed up his steps. The kid was getting rather close to the edge of the walks and wasn’t looking where he was going.

“Ben?!” A frantic mother’s voice sounded. “Ben, where are you?!”

“Shit,” Dean mumbled to himself. He kept his eyes on the child as he began to sprint to save him from falling into the water under the ships docked. Stepping into the water and falling under was certain death. Not just for the child, but for anyone who dared to save him, as well.

“Ben!” Dean heard the mother’s panicked shriek as the child took one step over the edge.

Dean caught him by his arm and dragged him back up and into his chest. The boy wailed and started crying.

“Sh, it’s okay, I’m sorry for scaring you, Ben, it’s okay,” He said in a soothing voice.

“Oh, my gods!”

Dean turned just in time to see Ben’s mother run over to him with her arms out. He gave the kid over to her quickly, and knowing how people felt about him he immediately backed up to a safe distance.

“I’m sorry,” Dean put his hands in his pockets, “He was getting rather close to the edge and I wouldn’t have wanted to see him go under.”

The mother cradled the crying child into her, rocking and shushing him. She looked up at Dean with watery eyes. Recognition set into her features and she tensed up. Dean took another step back.

She noticed and Dean saw some of the tension melt away.

“Thank you,” she whispered. Dean flashed his most charming smile at her and tipped his hat.

“Of course,” He said, nodding at the child, “He’ll be alright?”

She nodded, speaking slowly and choosing her words carefully, “I’d say so.”

Dean nodded and gave the mother and her child some time to settle down before he put his hand out, “I’m Dean Winchester.”

“I know.” Her eyes narrowed at Dean’s hand.

He retracted it, still giving her a genuine smile, “I take it you're not a fan, then?”

Dean saw her frown, “It’s not that, I—” She stopped herself and shifted Ben in her arms. He wasn’t bawling like before, but he was still sniffling. “Lisa,” She said and put her hand out, turning her body so that Ben was farther away from Dean than her hand. “Lisa Braeden.”

Dean took her hand and gave her a firm handshake, “Nice to meet you, Lisa.” Dean saw Ben look at him. He dropped his hand from Lisa’s and looked at the boy. “Nice to meet you too, Ben.”

Ben sniffed and rubbed his eye. “Hi.” His voice was quiet and soft. Dean felt his chest swell.

“Hello,” Dean smiled warmly at him and he wasn’t surprised to see Ben return a small shy smile to him before hiding his face into his mother’s chest. Dean had always loved children, and children seemed to always like him in return.

The Captain reached into his coat pocket and pulled out a clean handkerchief, handing it to Lisa. “Here,” He offered. Lisa accepted it, furrowing her brows at Dean.

“How did you get him to smile at you? He never smiles at anyone but me,” She said, wiping away the tears and snot on Ben’s face.

“Why, I believe I can’t say. I’ve promised Ben here it’d be our secret,” Dean joked. Lisa’s mouth twitched up before she could help herself. She shuffled her feet before trying to give the handkerchief back to the pirate.

Dean shook his head. “Keep it, I’ve got enough.”

Lisa’s face was hard and critical when she looked at Dean, but when their eyes met they told another story.

Her eyes were older than Dean felt was possible. There was a sadness in them that made it hard for Dean not to ask her how he could help her. She was worried about something, and it made Dean want to offer her and Ben a safe place on his ship to live, away from whatever was causing her this distress.

She retracted her hand with the handkerchief and hoisted Ben up on her hip. “Well, thank you, Dean,” She rushed out, giving him a nod of her head. “We’ve got to be going now.”

“Of course,” Dean smiled again, but something pulled at his heart. He wanted to help the Lisa and Ben; they seemed like they needed something good to happen for them.

He hesitated for a second before saying, “I don't want to put myself where I don't belong, but… If you need anything, Lisa and Ben Braeden, I’d be happy to help. You know where I’ll be for the next few weeks.” He gestured to the ship behind him.

Lisa’s lips quivered before she nodded and turned, Ben in her arms, to leave. Ben looked over his mother's shoulder at Dean and waved goodbye.

“Captain,” Benny’s voice sounded from behind him. “Let’s get going.”

“Yeah, yeah. We have work we need to do.” Dean let Benny lead the way to the market as he watched Lisa and Ben disappear. Dean could feel a slight disappointment, but with what he wasn’t sure.

~  ~  ~

“Sam!” Dean called up to his brother just as Sam had done earlier. “Get the swabs and tell them to get down here to help Benny with counting and documenting the inventory we have. When they’re done, they can take the rest of the night off and in the morning we start repairs.”

The sun had set and most of Dean’s higher ranking crew had left the ship to go out to the bars and the taverns.

“Aye aye!” Sam called, dashing back to get the swabs.

“I’m going to-” Dean trailed off as he saw a young man stumbling across the quad in the middle of all the port houses. He was dressed rather formally, with a dark blue suit and a beige trench coat. His hair was messy, his shirt wasn’t tucked in right, and he was beautiful.

“I’ll be back,” Dean told Benny as he walked away towards the young man. He heard Benny scoff out a laugh.

Dean continued to watch the boy stumble and look around as if he was afraid of being spotted. Speeding up his pace, he jogged to catch up to the dark haired beauty.

“Excuse me,” Dean called out, the boy stopped and kept his eyes on the ground.

“Yes?” The boy responded, his voice was deep and gravelly, albeit a little shaky as well. By how he was looking Dean came to the assumption he was a streetwalker or a courtesan.

When Dean came to a stop, he was able to really take in the young man’s appearance. To put it bluntly, it looked like he’d just been fucked in a back alley. And the state of his voice only helped to bolster this thought.

Dean dug into his pockets and pulled out the gold in his pocket. “I’ll give you...” Dean stopped to count, “Seventeen gold to spend the night with me.”

The young man’s head snapped up looking absolutely scandalized. Dean had a moment of uncertainty, thinking that this man was, in fact, not a prostitute. Could you blame Dean for coming to that conclusion, though? He was stumbling around with his hair and shirt askew, his face looked flushed and his lips were red and chapped.

Dean caught the man’s eyes and his expression changed. He seemed to consider this, hesitating before reaching his hand out and grabbing the gold. Dean smiled charmingly at him.

“What’s your name?” He asked.

“C-Cast-,” he stopped short before responding shyly. “Cas.”

“Well, Cas, I’m glad to meet you. Will you follow me?” Dean asked, giving his hand to the shorter man. Cas took it slowly and allowed himself to be led back towards the Impala.

Dean felt Cas stumble before stopping. “What?” He said, almost sounding like a whimper. Dean smirked. His reputation sure was one of the Gods.

Dean turned to look at the boy, “I won’t hurt you.”

Cas flicked his eyes onto Dean’s for a second before returning them back to the ship. The Captain gave him some time to reconsider if he wanted to, but Cas began to follow Dean again.

They walked past the swabs obeying Benny and Sam’s orders to check inventory. Cas’s hand clenched around Dean’s.

Dean pulled Cas closer to him and they ascended the stairs to get onto the deck of the ship, he slipped their fingers together. “Do you want someone to carry your books for you?”

Cas shook his head, “I’m fine.” But his voice betrayed his statement.

“You seem nervous,” Dean noted. 

“I-I’m on the Impala 67 with Dean ‘ _The Righteous Man_ ’ Winchester. You’re the _Pirate King_ ,” Cas said quietly, fumbling over some of his words.

Dean chuckled, “Not tonight.” He stopped and opened the door to the cabins, letting go of Cas’s hand to gesture him to go first. When he hesitated, Dean smiled warmly at him. “I won’t do anything you don’t want me to do.”

Cas eyed the dark narrow passage and then took a deep breath. “Okay.” He started down to the Captain’s cabin, Dean following closely behind.

“It’s right up here,” Dean motioned, pointing at the door on the left. Cas nodded and pushed it open, gasping, again, at the interior.

“I thought…” He started, trailing off.

“You thought what?” Cas jumped slightly when he felt Dean’s breath right in his ear. Dean pushed against his back to get him to move in further.

“I thought it’d be dirtier.” He took a few steps forward, giving Dean enough room to walk past him.

Dean laughed and shook his head, “I keep my baby in pristine condition. And I never get my cabin dirty.” He shot Cas a sly smile. “Well, not in any way you can see.” Cas caught his eye before looking awkwardly at the ground. “You can put your stuff down anywhere you want.” Dean gestured around his room with a sweep of his arm.

Cas nodded and placed them down on a chair next to Dean’s desk. After that, he stood there awkwardly, fidgeting with his hands.

“Would you like a drink?” Dean asked. Cas looked at him and shook his head.

“I don’t drink,” he said, shrugging his shoulders. Something Dean found adorable.

“Virtuous,” Dean joked, considering what they were about to do. There was a moment of silence before anyone spoke. Dean took that time to finally really process Cas.

His hair was black and messy, but Dean had to admit the kid pulled off the bed-head look. He had the bluest eyes Dean had ever seen, and the most attractive lips Dean could ever remember laying his eyes on. His clothes were baggy, hiding his real frame. It made Dean wonder how small this boy really was.

“Well…” Cas spoke, awkwardly taking a hesitant step forward. Everything Cas did seemed endearing to Dean.

Dean decided to take charge and walked over to Cas, cupping his cheek. The corner of his mouth twitched up when Cas's eyes fluttered as Dean put his arm around his waist. He pulled Cas flush against his torso and couldn't help the toothy grin that brole out across his face when Cas gasped, “Oh.” And his hands came up to rest on Dean’s chest.

Dean said, “You’re cute. Especially when you’re nervous.” He removed his hand from Cas's face to grip his hips. Then Dean brought his lips down to brush against the younger boy's. He was met with hesitancy. But that didn't deter Dean. He pressed his lips to Cas's gingerly, as to not rush things with him. Dean wasn't going to lie — especially not about something as vulnerable as sex — he wanted to make this night wth Cas last. Not for any reason he could name, though.

Dean was surprised when he felt Cas slide his arms around his neck to deepen the kiss. He didn't let that distract him and instead he opened his mouth, swiping his tongue along Cas’s bottom lip.

“Oh,” Cas gasped again, opening his mouth for Dean to sneak his tongue in. And Dean absolutely did. He hungrily dove his tongue into Cas’s mouth, pushing against Cas's tongue in hopes of eliciting gorgeous noises from those beautiful lips.

He got so carried away with making Cas moan, he forgot to breathe and had to pull away for air. Dean didn't move far, though. He couldn't really; not with the way Cas was gripping his jacket to pull himself closer. A chuckle escaped Dean as he pecked Cas's lips before resting their foreheads together. “Gods,” Dean panted, pulling Cas with him as he walked back towards the bed. It was surprising to Dean how turned on he was getting by this kid. And how receptive Cas was sure wasn't doing anything to stop his building arousal.

When Dean felt his calves hit the bed he sat down and pulled Cas onto his lap, kissing his way along Cas’s jaw to his neck to nip at his pulse point. The urge to mark up Cas’s neck was almost overwhelming. But he pulled his lips away, making the boy whimper, “No.” Dean was surprised at this and found himself becoming lightheaded from how much blood was rushing below his belt.

Cas’s hands threaded into Dean’s hair and urged him back towards his neck again.

“You don’t care if I mark you?” Dean asked, nuzzling the soft skin of Cas's neck.

“No,” Cas said, a little breathless, tilting his head back to expose more of his neck. Dean felt himself becoming harder as he restarted his assault on Cas’s neck, marking him lightly. He didn’t want to give him anything that would last more than a few days because Dean knew that on the few instances when he picked up someone off the streets, he didn’t want to see the evidence of another having slept with the same lover. And he didn’t want to wreck Cas’s chances of finding another person to sleep with and have the consequence be he’d go hungry or worse. And as much as the thought of someone else taking Cas like he was bothered Dean, he was not a monster.

Dean continued to suck, nip, and kiss his way over Cas’s neck, noticing that the boy in his lap was  _incredibly_ responsive. Dean could feel the Cas's erection pressing into his abdomen through the slacks he was wearing. And _holy Gods_ was Cas hard.

Cas whimpered, squirming against Dean and Dean smiled, talong that as a sign Cas wanted more. He made quick work of unbuttoning Cas’s shirt sliding it off his shoulders along with his coat. It pooled on the ground by Dean’s feet and Dean was now able to see how bloody _young_ this kid was. He couldn’t be near old enough to be doing this.

“Cas,” Dean said sternly, making the younger boy frown and look just a bit guilty. “How old are you?”

“I’m eighteen,” he rushed out. Dean looked at him skeptically. Cas pouted slightly. “I swear. I’ll be nineteen in five months.”

“Are you…” Dean’s eyes widened in understanding. “Are you a virgin?” Cas looked down sheepishly. That was answer enough for Dean and he began to push Cas off his lap. “I can’t—” Dean began to tell Cas that he couldn’t do this to him. It wasn’t right. But he was stopped short by the death grip Cas suddenly had on his shirt’s collar.

Cas looked at him with panic and urgency in his eyes, his voice matching them, “No, please. I want this. I _need_ this.”

“Cas…” Dean trailed off. 

“You’re not that much older than I am, Dean,” Cas continued to protest. “You’re only six years older.”

“It’s not about age. I just… I’ve got so much more experience than you. I…” Dean rubbed his eyes in frustration. “I… I can’t hurt you—"

"You wont," Cas rushed out.

Dean snorted before replying, "Do you even know how sex works?"

"In theory," Cas whispered, looking up at Dean through his lashes. 

Dean raised his eye brows incredulously. "In theory?" He repeated. "Look, Cas—" 

"Please?!" Cas cried, shifting his hips against Dean's again. "I can't tell you want this, too, Dean."

"It's not about whether I want this or not," Dean said softly. "It's about that this is your first time. A-and your first time should be with someone you love and trust and…” he trailed off.

Cas looked into his eyes and Dean could see the sadness and scaredness in them. “My father is going to marry me off tomorrow — to a _woman;_ I don't like women in that way. And sh-she'll probably be two times my age. I don’t want my wedding night to be my first time. Especially not with a woman.” 

Dean swallowed. “Cas,” he couldn’t look into those brilliant blue eyes anymore. “I don’t know if I can.”

“Please, Dean,” Cas’s voice was desperate. Dean didn’t respond, thinking everything over. But Cas gripped onto the collar of his jacket and rocked into Dean’s hips. “ _Please_. Whoever I’m married to… She’s not going to care about me. She’s just going to use me.”

That was it for Dean. He was not going to let this boy be _sold_ and  _used_. He slipped his hands under Cas’s thighs and stood up.

“We’re going slow.” He brought them both to the center of the bed on his knees before laying Cas down on his back and settling himself between the boy’s legs. “If we’re going to do this, we’re doing it right.”

“Yes,” Cas whispered breathlessly, pulling Dean in for another kiss.

Dean used one of his arms to support his weight so he didn’t crush Cas, while the other splayed itself across Cas’s exposed torso, moving up and down, wanting to touch as much as the boy as he could. He wanted to make Cas’s first time so good for him. He wanted to make Cas never forget this night with the Pirate King.

“Dean,” Cas’s voice came out high-pitched and broken. The way Cas was already so turned on and needy, just by being kissed and lightly touched, was amazing to Dean. And how many small noises Cas made into Dean’s mouth turned Dean on, in return.

Dean stopped and sat up on his knees, watching Cas open his eyes halfway and wine as he grasped out at thin air for Dean.

Smirking, Dean moved his hands to undo Cas’s trousers, earning a pitiful whine from the boy; he looked so debauched that Dean was almost certain he wouldn’t be able to form words at the current moment.

Dean gingerly pulled Cas’s pants down, taking a moment to enjoy how perfect Cas looked with just the tight-fitting white drawers on before sliding them off and tossing them behind him somewhere. Turning his eyes back to take in Cas’s newly exposed skin he inhaled sharply.

“Damn, Cas,” Dean smiled. The boy in front of him was the complete opposite of him — downstairs size wise, that is. He was rather… Small. Not that Dean minded, though. He decided then that preferred when his partner was less than average, actually. But Cas was also completely smooth. Dean smirked, and looking up to the boys face said, “You’re boyish all around.”

Cas looked hurt and had to take a moment to catch his breath before responding. “Is that supposed to be a compliment?”

“I wouldn’t dare mean it as anything else,” Dean chuckled, ridding himself of his top layers of clothing. He heard Cas gasp; a sound that was half shock and half concern.

“Dean?” Cas asked, staring at his scar covered chest and arms.

“Life of a pirate,” Dean said. And it wasn’t a lie… Not completely, anyway. Cas’s eyes scanned his torso, his pupils becoming larger.

“What’s that?” He asked, pointing to the tattoo Dean had on his chest. It was a pentagram with what looked like the rays of a sun circling it.

“It’s my pirate symbol, everyone on my crew has it,” Dean answered. He leaned down and kissed Cas, distracting the younger with a tongue in his mouth. Cas smiled into the kiss and then slid his hands down Dean’s chest before coming around to feel the man’s back. Dean had to break the kiss to allow Cas a sharp, pitched inhale.

“ _Oh_. You’re so…” Cas’s breath caught. “You’re so firm.”

“Is that supposed to be a compliment?” Dean joked, reveling in the feeling of Cas’s hands on his back, fingers kneading his muscles and nails dragging over his heated skin.

Dean shifted himself and pushed his leather-clad thigh against Cas’s bare length, making the boy moan loudly and arch his back. “Do that again please,” Cas just about begged. Dean breathed deep, trying to keep his cool.

“Such nice manners,” He laughed, pushing into Cas’s member with his thigh again. “Such an _angel_.” Dean was surprised at how loud Cas yelled out at the contact again. Cas’s hand came over his mouth and he looked at the man above him with wide eyes. Dean shook his head, grinning and said, “You don’t need to be quiet.”

“But your crew?”

“My room is pretty much soundproof,” Dean said, pushing his thigh into Cas’s erection again. Cas shivered and his hips bucked into Dean involuntarily, another moan being ripped from his lips. “Cas, fuck,” Dean gasped. At the use of the curse word, Dean felt Cas shudder again and dig his nails into his back. The Captain took a deep breath, closing his eyes at the surprisingly pleasant sensation. But he stopped his movement against Cas in favor of sitting up again.

“No,” Cas was just about crying. “Feels so good.”

Dean smiled internally. “Sh,” he soothed, undoing his own trousers and gracefully ridding himself of them and leaving him in only his drawers. “Gonna make you feel even better.” Dean ran his hands over Cas’s thighs, getting close to where he knew Cas wanted to be touched most, but gliding past onto his stomach. “Have you ever come before, angel?”

Cas shook his head, his eyes trained on Dean’s hands. “No.”

Dean looked pleased of that confession. He grabbed Cas’s hands and pulled him up and onto his knees before spinning him around so his back was pressed against Dean’s chest. He smoothed his palms over Cas’s stomach and then moved them to wrap around his torso.

“Put your hands on my shoulders and don’t move them,” Dean commanded, his mouth right next to Cas’s ear. A deprived cross between a whimper and a whine left the boys mouth. Dean gave Cas a few seconds to find a position comfortable enough for his arms before he moved his hands over Cas’s torso, never going lower than his hips.

Cas’s breathing was ragged and uneven, small and desperate noises left his mouth without any second thoughts. Dean lowered his head to kiss Cas’s neck.

“Oh! Dean,” Cas moaned loudly. Dean nipped at Cas’s neck and moved his hands up to play with the boy’s nipples. Cas’s breathing became loud and labored, his hands gripped Dean’s shoulders like his life depended on it.

“You want me to touch you?” Dean whispered into Cas’s ear. “You want me to take your cock in my hand and make you come?”

“Yes!” Cas all but screamed, “Yes, please, yes!”

Dean chuckled and moved his hand down to the small boy’s cock, liking the fact of how well it fit in his hand. Sucking back at Cas's neck and pinching his nipple, Dean pumped his hand over Cas’s member.

“Oh!” Cas screamed, his hips thrusting into Dean’s hand erratically. Dean clicked his tongue.

“That won’t do,” He mumbled, moving the hand that wasn’t on Cas’s length to Cas’s abdomen, holding him still so his hips couldn’t move as Dean pumped his hand.

“Dean,” Cas breathed out, his hips still trying to thrust into Dean’s hand. “Oh, Dean.”

“I love it when you say my name,” Dean bit down lightly on Cas’s ear lobe. “Say it again.”

“Dean,” the boy moaned.

“Again!”

“ _Dean_!” That was it for Cas, he came with a scream, “Oh, _yes!_  Dean.” Cas slumped against Dean as he was jerked through his orgasm.

“You feel good?” Dean whispered into Cas’s ear, slowing down his hand as he felt the muscles in Cas’s stomach relax.

Cas nodded with his eyes closed, “Yes. Yes Dean, yes.”

In a sudden and surprising moment of feeling like he needed to stake his claim on Cas, Dean growled and pumped his hand. “Who made you feel good?” Dean gave another few quick pumps of his hand, causing loud, needy screams to leave the boys lips.

“You did! You did, _Dean_!” Cas jerked back against Dean, trying to get his cock away from Dean as one of his hands came to dig its nails into the skin of Dean’s forearm while the other stayed on Dean’s shoulder.

“Good,” Dean purred, taking his hand off of Cas’s length and running his hands over Cas’s skin. He held Cas up against his front, massaging the boy's stomach. Cas panted, his head falling back onto Dean’s open shoulder. 

Dean continued to do this until Cas’s breathing settled down and he wasn’t digging his nails into Dean.

“Are you good now?” Dean asked.

Cas swallowed, making his Adam’s apple bob, and nodded. “I think so.”

Dean gently scooped Cas up and laid him back down on his back. Cas’s face was rosy from all the returning blood, and his bottom lip seemed swollen from biting it between moans. Dean scanned his face, taking in all the detail: the downward slope of his nose, the slight bump just above and to the right of his Cupid's bow of his lip, the almond shape of his eyes, and the plumpness of his cheeks. He was absolutely beautiful, to Dean, honestly.

Cas’s eyes blinked slowly, still coming back from his pleasure trip. His neck was peppered with light pink spots and his mouth hung open. Dean wanted Cas to not regret this night. He leaned down and kissed him lovingly. Cas responded rather quickly, yet with sloppier precision. But it didn't bother Dean in the slightest.

“Thank you, Dean,” Cas whispered against his mouth. Dean smiled fondly at him and kissed Cas deeply before moving to bury his face in the crook of Cas’s neck.

“Of course,” He said, inhaling and smelling a field of flowers and vanilla soap.

“No fair,” Cas said a few minutes later, pushing Dean up.

“What do you mean?” Dean asked, slightly worried that Cas wanted to leave.

“I’m completely undressed whereas you still have your drawers on.” Cas pointed to Dean’s clothed groin. Dean felt himself smile in relief.

“Sorry,” Dean chuckled, not really meaning it. He took them off and sat on his heels in front of Cas.

“Oh, my,” Cas gasped, eyes widening at how big Dean was. “You weren’t lying when you said you weren’t small.” Cas had a hint of fear in his voice.

“I won’t do anything you don’t want me to,” Dean reminded Cas, putting his hands on Castiel’s spread thighs and rubbing soothing circles into them with his thumbs. Cas swallowed again and pushed himself up onto his elbows.

“May I…” He hesitated, biting his bottom lip and blushing madly. “May I touch you?”

Dean smirked at the innocent boy. “Angel, you can do just about whatever you want.” Cas blushed at the nickname but nonetheless pushed himself up into a sitting position. He looked at Dean with wide eyes.

“What…” Cas trailed off as Dean gave him a fond half-smile and took his hand in his own, guiding it to his manhood. Cas bit his bottom lip again as he wrapped his hand around Dean’s shaft.

“Now just move your hand like I did with you,” Dean said, running his hand through Cas’s hair gently.

Cas closed his fist more firmly around Dean’s girth, “Like this?” He asked. When Dean nodded, he started to slide his hand along the length. “You're so hard.”

“That usually happens when a guy gets turned on.” Dean inhaled sharply, “Fuck, Cas,” he whispered, letting his eyes close and his neck become loose.

“It feels good?” Cas asked with a hint of anxiousness in his voice. Dean nodded and tugged lightly on Cas’s hair to help get his point across. Cas started getting more confident with his motions and sped his hand up. He brought his other hand up to also grip Dean’s shaft, drawing a groan from Dean’s lips.

Now, Dean Winchester always prided himself on his stamina and endurance in bed. But this kid was definitely threatening to screw up his resolve. He opened his eyes and saw that Cas was wearing a look on intense concentration as he moved his hands along Dean's shaft. Dean also saw that he was starting to breath heavily and get hard again. Putting his hand on Cas’s, he stopped him.

“Did I do something wrong?” Cas asked, worried. Dean shook his head and pulled the younger boy up onto his knees.

“Absolutely not, but this is your first time and I want to make it so good for you,” Dean said, his words coming out breathier than he would've liked.

Cas looked down at the bed and scrunched his eyebrows together, “How…" He hesitated. "How often do you bring people in here?” Cas’s voice was small and unsure.

“I’m not a virgin,” Dean stated. A dark emotion passed through him. It came from some part that he thought he had been able to leave behind long ago. He shook his head clear of the awful memories and he composed himself again. “But I’m not promiscuous either. If I see someone I find attractive usually I'll take them out for a drink before bringing them back here or to a room at an inn. Only if they pass my further inspection.”

Cas looked up at Dean, “What was different about me?”

“You want honesty?” Dean asked, nudging Cas to lie down again. He ran his hands down the sides of Cas’s frame as the boy wrapped his arms around Dean’s neck.

“Yes.”

“I don’t know,” Dean said. Cas smiled a little and moved his eyes down to Dean’s chest and stomach. Dean felt himself smirk as Cas slid his hands down from his neck to feel the pirate’s muscles.

Dean tilted his head down to be able to kiss Cas as his hands found Cas’s hips. In a swift motion he pulled their bodies together. Cas gasped at the contact; while his mouth was open Dean took this opportunity to explore Cas’s mouth.

Cas’s own tongue rubbed against Dean’s hesitantly at first, but when Dean tightened his grip on Cas’s hips, the younger boy did it again. Their tongues wrestled against each other — with Dean making sure not to overwhelm the boy.

“Dean,” Cas said breathlessly, “I need air.”

“Right, sorry,” Dean said, beginning to get breathless as well. He rested their foreheads together and closed his eyes, relishing in the feeling of being in such close and bare proximity of Cas.

When Cas smiled and tried to kiss Dean again, Dean only gave him a small kiss. “Can you turn around and get on your hands and knees?” The older man asked but hesitated in letting go of the younger’s hips. “Are you sure you want to go through with this? We don’t have to.”

Cas nodded his head, “I want to,” He said, pushing away from Dean, “I-I do… But go slow?”

Dean looked into Cas’s eyes, searching for any doubt, but couldn’t find any. “Of course, Cas,” Dean responded, letting go of the boy’s hips. “I don’t want to hurt you.”

Cas smiled before turning around and getting on all fours. Dean could see he was blushing a little, so Dean rubbed his back soothingly.

“You’re perfect,” Dean said. And he meant it. “Reach into my nightstand and grab the bottle of oil, will you, angel?”

The boy nodded and did as asked, handing the bottle back to Dean who opened it and dipped his finger in, letting it warm up on his hand before touching Cas’s entrance.

Cas jerked forward and yelped in surprise. “Sorry,” Dean retracted his hand. “Sorry, I should’ve warned you.”

The boy let his head hang down for a second before speaking, “No, it’s okay. It felt…” Cas stumbled on the words, embarrassed. “It felt good. I just wasn’t expecting it.”

Dean chuckled and moved his hands to massage the back of the small boy’s thighs, slowly making his way up. He didn’t move back to touch Cas as fast as he had before, but instead took his time and made sure Cas was relaxed.

And when Dean did finally touch Cas again, a small gasp of surprised pleasure left the boy’s lips.

“Angel, I need you stay relaxed, okay?” Dean said, moving his finger in circles against Cas’s rim, earning small and high-pitched noises from the boy.

“Yes,” Cas breathed out, his arms trembling. Dean felt a swell of pride in his chest that he was the one to make Cas feel this good. He pushed on Cas’s upper back.

“You don’t have to keep yourself up on your arms,” Dean said lovingly, “You can lie down.” Cas nodded and let himself all but collapse onto the bed, sighing in relief when he didn’t have to concentrate on keeping himself up. “Are you good?” Dean asked, making sure he was okay to start opening Cas up.

Cas nodded, pressing back against Dean, “Please,” he whined. Dean didn’t need any more encouragement to try and push his finger in. Oiling up his digit and pressing it into Cas, Dean felt him tense up just slightly before Dean rubbed the boy’s back soothingly.

“It’s okay, Cas,” Dean soothed, “I’m gonna take good care of you.” Cas relaxed into Dean’s touches and felt Dean very slowly push his finger into him.

“Dean,” Cas gasped in pleasant surprise when he felt Dean crook his finger just slightly.

“Feel good?” Dean asked, not moving any part of him until he got the okay from Cas to do so.

“Do that again,” Cas breathed and then buried his face into one of Dean’s pillows, muffling the sounds he made as Dean moved his digit inside him.

“Let me hear you,” Dean said, pulling his finger out before pushing it back into Cas. “Tell me what you’re feeling.”

Cas wasn’t able to move for a second. “I feel on fire,” He said, his voice breaking. “I feel… I feel… Dean!”

Cas’s back arched when Dean added a second finger; he hadn’t even felt any pain with the way Dean did it.

“What do you feel?” Dean insisted that Cas answer him.

“I feel like I’m going to melt.” Cas’s voice was low and hoarse. He couldn’t think very well right at the moment. “Dean, I can’t… I can’t…”

Cas didn’t need to finish, Dean understood what he was saying. And he didn’t blame the boy for not being able to complete his sentences. After all, Dean was a master with pleasuring his partners, and Cas was painfully new to all these feelings.

“It’s okay,” Dean shushed him, “Just focus on my voice.” Cas nodded and focused on Dean’s praising words; calling him perfect and saying how beautiful he looked.

Dean scissored his fingers open, going slowly to let Cas adjust. He felt his own aching cock between his legs, but he was more focussed on Cas and making sure he was taken care of.

“Are you okay if I add another?” Dean asked breathlessly, greatly turned on by all the sinful noises the virgin below him had been making.

Cas pushed back into Dean. “More,” He whined.

“Alright,” Dean said under his breath, dripping more oil onto his fingers to make this as painless as possible for Cas.

The noise Cas made when Dean did add his third digit was almost enough to make Dean come right there. It was a mix between a sob and a scream. And it was extremely arousing to hear.

“Dean,” Cas sobbed out, “More, please!”

By the powers did Dean want to give this angel all that he asked for, but he knew he couldn’t; not just yet. He spread his fingers in Cas to compensated, drawing a broken sob from the boy’s chest. Dean loved how vocal Cas was becoming; a thought of how fantastic Cas would sound when Dean was finally able to fuck him flew through his mind and he groaned loudly.

Cas matched his groan with a cry, too. Looking down at his face, Dean saw that there were tears coming out of Cas’s eyes.

“Do you need me to stop?” Dean asked, already beginning to pull his fingers from Cas.

“No!” Cas yelled with an impressive pitch.

Dean felt his cock become insanely hard and he fucked his fingers back into Cas. The tears that leaked out of Cas’s eyes made Dean grin with satisfaction. Dean, of all people on this big blue earth, was the reason for Cas’s moans and groans, sobs, whimpers, and pants. Dean was the reason for Cas’s pleasured noises. Holy fuck did that turn him on.

It made it hard for Dean continue stretching Cas instead of fucking him into the mattress. But Dean favored not hurting the young boy over satisfying his own aching cock.

“Dean,” Cas panted. “Dean, _please_ , more.” The taller man shushed the boy and added a fourth finger, deciding that after this one, Cas would be ready. “Please,” Cas sobbed, his hands fisting the sheets below him and his knuckles turning white. “Please, Dean… Please!” The younger boy’s voice was wrecked. Dean slowed his hand down and pulled his fingers out. Cas whimpered out a sob at the loss of contact.

“How do you feel?” Dean asked, flipping Cas over so Dean could see his face. Cas’s lip was bleeding from how hard he’d been biting it. “Gods.” He leaned down and sucked away the evidence of broken skin and intertwined their hands.

“Please,” Cas cried, his chest heaving. Fresh tears made their way out of the corners of Cas’s eyes. “ _Please_...”

“Okay,” Dean peppered Cas’s face with kisses, telling him how amazing he looked between each one. He gave one last kiss and sat up to oil his manhood up thoroughly. “Tell me if it hurts, okay?”

Cas nodded his hands scrabbling to find Dean’s. The taller man interlocked one of his hands with Cas’s while he used the other to guide his length to Cas’s entrance. The shorter boy looked completely debauched and utterly ready to be ravaged.

Dean pushed into Cas, meeting resistance he stopped and took Cas’s other hand in his own and leaned down to nuzzle Cas’s neck. The taller man breathed out a shaky breath. “Fuck, Cas, you’re so tight.”

Cas moaned in response, prompting Dean to sink slowly further into Cas; but not before he lifted his head to watch Cas’s face while he pushed into the small boy.

“Does it hurt?” Dean stopped when half of his length was in.

Cas made the most blissed out face Dean had ever seen and gazed up at Dean with lust blown eyes. “No, feels so good.” His words were slurred, Dean couldn’t help but think how lovely he looked like this.

Dean continued to push in, watching Castiel’s face closely, searching for any signs of discomfort. When he bottomed out, he stopped and let Cas choose when he wanted Dean to start moving.

Cas bucked his hips and whined.

Dean began to thrust shallowly into Cas, expecting him to moan or whimper or something. But when Cas went limp — his legs falling impossibly more open — under Dean, the older man grew immensely worried he’d hurt the boy. Dean stopped to look at his face.

“Hah!” Dean let out a strangled cry. Cas wasn't hurt… If anything, he was on the complete opposite side of pain.

The boy’s eyes were glazed over and staring into Dean’s with adoration as fresh hot tears slid out. He was no longer able to grip Dean’s hands. The boy’s mouth hung open, and Dean could hear all of the dainty puffs of pitched breaths leaving him as he was pushed up on the bed with every thrust of Dean’s hips. Not to mention the heavenly little whimpers that came along with those thrusts.

“Feels that good, angel?” Dean asked, letting go of Cas’s hand to take the boy’s chin between his fingers, leaning down and kissing him briefly. “Fuck Cas, you’re so godsdamn tight.” Dean rested their foreheads together, finding Cas’s current state of pure bliss bloody arousing and really over-the-top adorable. “You’re gonna make me come.”

Dean thrust into Cas again and felt the boy spasm around him. He looked down just in time to see Cas’s small cock spurt thick white streaks onto his stomach.

“ _Cas_ ,” Dean’s voice was hoarse and he had to take moment to really process what had happened. “Did you come from just my cock?” Dean felt his own orgasm building quickly in his abdomen, the obscene noises Cas was making pushing him further over the edge. “Oh fuck! Shit, Cas.”

One last thrust had Dean burying his head in the crook of Cas’s neck and coming inside the blissed out boy. He had to take several minutes to calm himself down and catch his breath after that.

“Dean,” Cas’s voice was barely above a whisper, his entire body completely spent and absolutely humming with pleasure.

“I got you, Cas,” Dean pushed his own achingly pleasured body up and pulled out of Cas, making the boy whimper at the loss of Dean's cock inside him. The Captain kissed the boy before making his way to the bathroom to wet a towel to clean them both up.

When he was done, he scooped Cas up into his arms and settled them both under the covers, cradling the small boy into him protectively.

Dean watched Cas fall asleep in his arms, the boy’s breathing becoming even and his face relaxing.

The Righteous Man kissed the top of the angel’s head and smiled, falling asleep to the sound of the boy’s heavy snores.

 


	2. Chapter Two

**Summary for the Chapter:**

> Dean has scars. Both physical as well as mental and emotional. He's got a troubled past that could leave a person on a dangerous path. Luckily for him, he has his family to help him. 
> 
> But you have to remember, family doesn't end with blood. And it certainly doesn't start there either.

**Notes for the Chapter:**

> Alright, this chapter gets pretty heavy. There's explanation of Dean's past and it may get triggering for some people. 
> 
> Past TW: Rape, suicidal ideations, child abuse, child rape, torture.  
> Present TW: Child abuse (emotional and physical) 
> 
> Some fluff (hopefully) between Dean and Cas at the end, however!

Chapter Two

_September 19, 1692_

 

Dean woke up the next morning with Cas still snoring lightly in his bed. During the night they’d moved and Cas was using Dean’s chest as a pillow while Dean kept one arm around him protectively, the other was intertwined with Cas’s hand.

He had to admit, this was a rather pleasant way to wake up. For just a split second, Dean saw himself waking up like this every morning next to Cas.

But that life wasn’t for _The Righteous Man._ He’d chosen a path that he couldn’t stray from. It was the family business, now.

Dean shook his head clear of the thought and gently untangled himself from Cas, making sure to cover the boy back up with his quilt. He took a moment to admire Cas’s sleeping form. The pirate’s stomach fluttered while looking at the boy who looked like an angel... So peaceful and serene.

Finally, Dean was able to tear his eyes off Cas and he headed towards the bathroom connected to his room to shower and get dressed. A routine that usually took ten minutes. But Dean was done, turning the water off, stepping out and grabbing a towel to dry himself in six. He slung the towel around his neck and walked back into the bedroom. Cas jumped slightly when he walked in.

Dean smiled at him. “Good morning,” Dean’s voice was cheery and light. Cas smiled at him before noticing Dean was naked and wet. His eyes traveled down Dean’s body before stopping at the older man’s groin. Pride swelled in Dean’s chest. “Admiring the view?” he joked, walking over to his dresser to grab some fresh clothes. Dean turned, careful not to show his back, and heard Cas speak.

“Even when you’re not hard you’re still huge.” The boy's voice was quiet and laced with uncertainty.

“Thank you.” Dean looked over his shoulder at Cas, smirking. Cas’s eyes found Dean's again and he blushed, pulling the covers up around him further. “Are you cold?” Dean asked, stepping into a pair of drawers, then pants and sliding a baggy white shirt over his head.

Cas shook his head, “No, it’s not that. I’m just… sore, a little.”

Dean swiveled to face Cas, “Do you want a massage?” He gave Cas a fond smile as he sat down on the edge of the bed, leaning over the boy bracing himself on his arm. Cas shook his head and tried to push himself up onto his elbows, letting out a soft sigh as he did.

“It’s not a bad kind of sore,” He blushed again, “I kinda like it.”

Dean almost laughed but thought better of it. “Where do you feel it?” He asked, already having an idea of where Cas was feeling it.

“My lower abdomen, and, I mean…” Despite not being a virgin anymore, this boy still defined the word. “You know…?”

“I do,” Dean said, smiling again at how charming and angelic Cas was. “Other than sore, how do you feel?”

Cas took a moment to contemplate this before answering. “My back feels kinda sticky.”

Dean chuckled, “That’s my fault. I laid you down right where you came the first time.”

“Oh,” Cas blushed again.

“Do you want to take a shower?”

Cas nodded, “Yes, thank you. That would be wonderful.”  

“It’s right through there,” Dean pointed, getting up from the bed and walking to his towel closet.

Dean handed the towel to Cas and watched as he covered himself with it before getting out of the bed.

“You don’t have to cover up, angel. I _have_ already seen you naked.” Dean walked back over to the bed and pulled off the soiled sheets, looking at the stain Cas had made. “That’s an impressive stain if I’m to be square.”

Cas looked absolutely mortified, “I’m sorry.”

Dean chuckled and threw the sheets into his soiled clothes basket. “No need to apologize.” He smiled reassuringly at the boy. “It was actually bloody arousing.”

Cas blushed, yet again, bright red. “I-I’m going to take my, uh, shower now… If that’s okay?”

Dean nodded. “Make yourself at home.”

When Cas was out of sight, Dean grabbed another pair of bed sheets and made up his bed in no time, calling to Cas that he was going to go on deck to check on some things. He made his way on deck and stretched himself out, breathing in the honest air. Now that he could mention it, he was a little achy as well. But, like Cas said, it was a good feeling. Dean couldn’t remember the last time he’d come that hard.

“Captain!” One of his mates came running up to him with Sam trailing behind.

“Ash? What is it? What’s happened?” Dean asked, immediately going on the defense.

“Dean,” Sam said quietly, catching his breath, “The boy you bedded last night...” Sam had to stop and catch his breath again.

“It’s Castiel,” Ash said, terribly out of breath. “His father…” Ash couldn’t finish.

“Dean,” Sam coughed, “He’s the son of Michael Novak.”

The Pirate King was out of words. Michael Novak… The Governor of the city of Heaven, and the most adamant citizen Dean knew of for _The Righteous Man_ ’s arrest.

Dean Winchester had just deflowered the virginal son of his worst enemy.

~  ~  ~

The Captain was back in his cabin and waiting for Cas to get done with his shower. He had to hear it from the boy himself.

A few minutes later, Cas came out, his towel around his waist and his hair dripping.

Not beating around the bush, Dean spoke. “You’re the son of Michael Novak?” Cas looked startled for a second before gripping the towel around his waist and nodding. Dean closed his eyes in frustration. “Why didn’t you tell me?” He looked into Cas’s eyes.

“I’m sorry,” he squeaked, “I didn’t think you’d go through with it if I told you.”

“You’re bloody right I wouldn’t have!” Dean exploded, making Cas flinch.

“Dean, I...” Cas sounded like he was about to cry, “I’m sorry.” Cas had to know what it meant for the pirate if Michael ever found out what he had done to his son. Dean would be hanged. Michael would make sure of that, and his crew would be in jeopardy of being jailed. The man had to calm himself down before he spoke.

“Nay,” Dean sighed, “ _I’m_ sorry. I didn’t mean to scare you.” He took a careful step towards Cas. “Your father can never find out.”

Cas nodded, “I wasn’t planning on telling him.”

Dean shook his head. “You don’t understand. This isn’t about me. You have no idea what he would do to my crew if he found out.”

Cas’s lip quivered as he spoke, “I understand.” He nodded curtly. Dean walked over to Cas and traced over his bare shoulders lightly before hugging him.

“I’m so sorry. I should have never done what I did last night.”

“I don’t…” Cas pushed Dean away to look him in the eyes. “I don’t regret it.”

Dean nodded, “I don’t either. Not one bit. But…” He closed his eyes again, “I should’ve asked more about you.”

Cas slid his arms around Dean’s waist, pushing his face into the taller man’s neck. “Dean,” He spoke softly, almost a hint of terror in his voice. “May I ask something of you?”

Dean’s arms wrapped around Cas, almost holding him too tight. “Of course.”

“May I see you again?” Cas’s voice was soft and shook slightly. Dean took a deep breath; he wouldn’t admit it, but he was hoping Cas would want to see him again too.

“Yes.”

“Thank you.” Cas’s voice was warm against Dean’s neck. The two of them stood in the Captain’s cabin for a long while, embracing and comforting one another. Neither of them were really sure what they were being comforted for, but that didn’t stop them.

For now, they were content with just this.

~  ~  ~

“Are you hungry?” Dean asked, almost an hour after the big ordeal had happened. He checked his time keeper. “It’s about eleven AM.”

Cas’s eyes widened, “What?!”

“It’s about eleven,” Dean answered, looking the younger man up and down.

“No! I have to get home!” Cas looked at Dean with panicked eyes. “I can’t be seen leaving the ship.”

Dean set his jaw and nodded. “I’ve got you.” He led them out into the hallway and to a closet opposite his own room. Dean opened the doors and pulled out a heavy brown over coat as well as a brimmed hat with three feathers sticking out of it. “Put these on and I can escort you into town, you have to keep your head down and the collars up.”

“Okay,” Cas slipped the heavy coat over his own trench coat and then put the hat on his head. He patted the leather down and straightened the hat before looking up at Dean with wide eyes. “How do I look?”

Dean smiled at him while looking into his eyes, making Cas’s stomach flutter. “Like a real pirate.”

Cas smiled back before Dean took his hand in his and guided him to the main deck. “Sam, Ash, Charlie, Benny!” Dean boomed across his ship. Cas was in awe of how loud his voice was.

“Aye, Captain?” Cas heard the responses coming from different directions before he saw the named off people.

“Sam, you take care of things while I’m taking Cas back, get the swabs to work,” Dean said, “Charlie, Ash, Benny, you’re coming with me to better keep Cas’s identity anonymous. I take it you all know who his father is?” Everyone nodded. “Who else knows?”

“Just us, Captain,” the red-head woman said. 

“Perfect, keep it that way for now.” There was an edge in Dean’s voice that gave Cas the chills. He wouldn’t want to disobey him.

“Aye, aye.” All of them said in unison. Sam strode off. Cas wasn’t sure what he was doing, but it seemed important. The other three arranged themselves around Cas, enough to shield prying eyes, but not enough to make them suspicious.

Cas felt Dean grab his hand, holding onto him tightly and keeping him close to his sturdy frame. “Where can we go?” Dean asked, leading his team off the ship and onto the docks. “Keep your head down.”

“There are some woods behind my house,” Cas said, keeping his head down and focussing on his and Dean’s hand. “If we can get to there, I can get home safe and no one will know anything.”

“You’ll need an excuse as to why you’re late,” Dean said, “Do you have any idea what you can say that’s believable?”

“I can say I was at the library,” Cas said, as they approached the Ports Quad. “It’s happened before.” Cas heard Dean chuckle and he smiled to himself.

“Where do we go now?” Dean asked, coming to a slow stop when they reached the spot where the gate opened into the city of Heaven.

“Turn into the alley on the left up here,” Cas instructed, lifting his head up only slightly to see where they were. “It goes along the outskirts of town and leads out to the woods.”

“Okay,” Dean lead the way, never once letting Cas’s hand go. Something in which he was grateful for. It kept him focused and grounded.

It didn’t take more than fifteen minutes of silent walking in the group and passing whispers and gasps of, _“That’s the pirate ”_ and _“Dean Winchester ”_ from the hustlers trying to work their living.

No one from the crew seemed affected by it as much as Cas though. He didn’t know what it meant, but he didn’t want people to gawk and stare at Dean as he passed them. They didn’t know Dean. They only knew what they’d heard about him. None of them had to right to assume he was monstrous just because the rumors said he was.

Cas pushed the thought down and kept walking.

But Cas must’ve tightened his grip on Dean’s hand because the taller man leaned down just slightly, “It’s okay. We’re almost there.” He ran his thumb across Cas’s knuckles soothingly.

Shortly after, they came to the end of an alley and after some checking around, stepped onto the path leading into the woods.

“You can look up now,” Dean informed Cas, not letting go of his hand; not that Cas wanted him too. Dean was a comforting presence, and - maybe because the man took his virginity, maybe some other reason - Cas craved his touch.

Cas looked up and around, familiarizing himself with the surroundings. While doing so, he caught the eye of the red-headed woman; she smiled at him, her teeth showing.

“I’m Charlie,” She said. “Nice to meet you.” Cas was thankful for the interaction and smiled back at her.

“I’m Cas, it’s nice to meet you, too," he said. Charlie and Cas shared a moment of eye contact, making Cas’s shoulders relax and his grip on Dean’s hand loosen.

“How old are you?” Charlie asked, Cas was sure not meaning to pry, but it was almost coming off that way.

“I’m uh, I’m-”

“He’s an adult, Charlie. I wouldn’t fuck someone who’s not legal,” Dean shot her a playful smile. Cas again blushed at what a sailor mouth Dean had, but he could tell that even though his tone sounded joking, he was being honest.

“Shut up, ya scoundrel,” Charlie giggled before leaning into Cas, “He’s such a cutie.” Charlie winked and giggled some more when the two other men behind them laughed as well.

Cas smiled, feeling like he could talk to this girl. “I’d agree.”

“I think I’m adorable,” Dean said in earnest. Laughs were heard and Cas found himself looking up at Dean in adoration. He was not the man the rumors said he was. He wasn’t selfish or conceited. At least not with Cas. But the way he joked with his crew and was so obviously proud of his brother, it made Cas think he was _nothing_ at all like the rumors.

But, Cas had to take into account, he was a pirate. Some truth had to come from those rumors.

“How much farther?” The taller of the two men behind Cas tapped him on the shoulder and gave him a quick smile. Cas looked around and spotted his house between the trees.

“We can stop here,” Cas said, tugging on Dean’s hand.

“Finally,” the other man said.

“Oh, Ash, always a complainer, you are,” Charlie said, rolling her eyes.

“I have important work I need to get done,” Ash defended himself. “I’ve almost figured out a way to make our canons easier to target.”

“Okay, you three stay here while I take Cas to the edge of the forest,” Dean said, not commanding them to obey, but asking.

“Aye,” The three shipmates said in unison. Dean sent them all thankful smiles before pulling Cas with him to the edge of the forest.

They didn’t talk on their short trek, and if Cas were to be honest, Dean really didn’t need to accompany him on this walk. When they stopped Benny, Ash, and Charlie could still be seen.

Cas was glad Dean came with him though.

“Here we are,” Dean said, stopping and letting Cas walk around him to face the taller man.

Cas hesitated; he looked up at Dean and then at his house before speaking, “Come see me tonight?”

“I don’t know, Cas,” Dean said, tilting his head down just slightly.

“Please?” Cas snaked his hand up to the back of Dean’s neck, “My room is the one with the balcony on the east side of the house.”

“Cas,” Dean sighed. “I want to, believe me, I really do.”

“No one will know,” Cas said hopefully. “My father will be gone tonight, there’s a town meeting, and my mother goes to sleep at eight.”

Dean looked between Cas’s eyes before he smiled, “I’ll come.”

Cas grinned back at him, “Thank you.”

“Of course, Cas,” Dean said and leaned down farther. Cas got the hint and stood up on his toes to connect their lips. Dean was gentle and sincere in his kiss. Cas opened his mouth and tried to push his tongue into Dean’s mouth, but Dean pulled away.

“Dean,” Cas complained, only making the man chuckle.

“We have plenty of time for that tonight,” He said, cupping Cas’s face, “But right now, unfortunately, we do not.”

“You’re right,” Cas said, disappointed but quickly perking up thinking about seeing Dean again. Cas pulled away from Dean, “I’ll see you tonight?”

Dean smiled happily at Cas, “Absolutely.”

“Okay,” Cas finally pulled away from Dean and took off the clothing of Dean’s he was wearing and gave it back. He gave Dean a quick smiled before turning and jogging back to his house. He only looked back once to see Dean still standing and watching over him.

~  ~  ~

“This isn’t a game, Castiel!” Michael shouted at his son, throwing a lamp across the room.

“I’m so sorry father,” Cas pleaded, crying at the violence his father was exhibiting.

“You’d better be!” Michael lifted his hand and struck Cas across the side of the head, sending him sprawling onto the floor with a loud thud. Cas pushed himself up onto his hands and knees, trying to focus his vision. He was shaking and couldn’t see straight.

“Father,” He sobbed, falling back onto the floor, hitting his chin against the rough wood and feeling his teeth rattle. “I’m so sorry!”

Michael came over to him and yanked him up by his hair. “Don’t ever let this happen again, Castiel. Do you hear me? You missed the most important meeting of your life.This arrangement could have changed everything for Heaven and for _me!”_

“I’m sorry!” Cas had tears flowing down his face from the pain his father was inflicting upon him. “I’m so sorry! I won’t ever let this happen again, I promise!”

Michael scoffed and pushed Cas’s face to the floor. “You’re a disgrace to this family and a disgrace to the Novak name.”

“I’m sorry,” Cas wailed in pain, “I’ll do better!”

"You've just cost me the certainty of Dean Winchester's death," Michael sneered at his son, leaving the kitchen where he’d caught Cas getting breakfast. “Do you even understand how many years I've been planning this?"

"I got caught up at the library," Cas cried harder, his head pounding. "I'm truly sorry."

"You've just undone more than five years worth of sucking up and placating the King of the Royal Kingdom," Michael kicked Cas onto his back. "Crowley does not forgive or forget easily! You've very much just doomed this family and erased my chances of Dean Winchester's head in a jar!"

"Father," Cas wheezed. He started getting lightheaded and cried harder. A vicious cycle started after that.

"You're absolute rubbish," Michael said. "Pathetic." He left Cas on the floor, sobbing and head throbbing.

“I’m so sorry,” Cas sobbed before he blacked out.

~  ~  ~

All day Dean spent making small repairs to his ship where ever it was needed, his mind drifting back to Cas and being able to see him again tonight. Apparently, it was showing, because, after a meeting with the heads of staff on Dean’s ship, Charlie, Benny, and Sam cornered him.

“What is going on with you, Dean?” Charlie sighed, crossing her arms. “You paid no attention to that whole meeting.”

Dean laughed nervously, “Nothing.” He rubbed the back of his neck. “I’m fine. I’m just a little caught up with something.”

“Castiel,” Benny stated. He knew Dean better than anyone, really.

Dean sighed and leaned forward in his seat. “Cas,” He corrected. “But, aye.”

“Just because you’ve found a fun fuck doesn’t mean-” Sam started, but Dean cut him off.

“Shut up, Sam!” He almost shouted. “I don’t want to have Cas around just to fuck him.”

“Dean,” Charlie warned him. “You know you can’t get attached. It’s too dangerous.”

Dean sighed. “I know,” he whispered. Charlie came over to him and put her arm around his shoulders. “He’s just… He’s different... I don’t know.”

“Fuck, Dean,” Benny shouted. “You’re going to get yourself killed.”

Dean sneered at him, “You shut up, too, Benny.”

 _“Nay._ Dean, listen to me.” Benny came over to kneel in front of him. “He’s the son of _Michael Novak._ You can’t get involved.”

Dean snorted, “I’m kinda already involved. I… I took his virginity.”

“What?! ” Sam shouted, looking at Dean bewildered. “Did you know?”

Dean nodded slowly. “I did. I wasn’t going to go through with it. But he said he didn’t want his first time to be on his wedding night with someone that was only going to use him.” Dean looked up into his brother’s eyes. Sam blinked before frowning in understanding. Charlie rested her head on Dean’s shoulder.

“Oh Dean,” she whispered. Benny closed his eyes and dropped his head.

“You guys know,” Dean stated. “You guys know how terrible that is… You were there with me through all of the aftermath.”

“We know,” Benny said, looking back up into Dean’s eyes. “ _I_ know,” he whispered so only Dean could hear him.

Sam’s face contorted into a look of sorrow. “I’m sorry, Dean.”

Dean could feel his eyes become watery. “I couldn’t let that happen.”

Charlie nodded, “We understand. It’s okay.”

Dean started to cry then; his three best friends comforting him while his body shook with violent sobs.

 

Dean was only eight when it happened. His father sold him to a royal looking for someone to have around for whenever he needed to fuck. Dean was that someone.

Two months short of ten years. Dean spent _ten years_ in that awful castle: Castle Purgatory. He was kept locked up in his cell in the dungeon when he wasn’t tied down to the table in which he was assaulted over and over again on.

The person Dean’s father sold him to was an absolute monster. Once a day - minimum - he would come down into the dark floor below his dungeon with his guards and force Dean to be strapped to his “table of nightmares.” Once Dean was tied down and unable to move, he forced himself into Dean. No preparation, no reprieve, no regard for Dean’s well being.

Dean was only _eight_ , and the monster forced Dean to do whatever he pleased. The creature starved Dean to make him smaller; all the more better for the monster's pleasure.

When Dean was able to stop himself from making any noise - especially the screams of pain and sobbed pleas for the creature to stop - the monster had to come up with new ways to make him scream. He whipped Dean’s back, arms, chest, stomach - _everywhere_ \- to make Dean scream. There was a scar in his back that at one point had been a cut so deep his spine could be seen. An _“anniversary present,”_   as the creature called it.

By the time Dean turned fifteen, it had been long since he had lost hope of ever getting out. He often found himself dreaming and wishing for death. That’s when Benny showed up. He was also meant to be another slave for the monster, but Dean was taken almost every time, instead of Benny.

Dean was the abomination's favorite.

One day, Dean came back from his torture, bleeding profusely from an extremely harsh whipping and raping. Benny tended to Dean and when the monster came back again, he went in Dean’s place. When Dean came back from the brink of death, Benny told him that they were getting out together. No matter what, they were getting out.

Dean started crying. Benny held him close and muffled the boy’s cries. If the monster heard them, he’d come back and rape Dean again. The creature loved it when his toy was in pain. He got off on it.

It took a year for them to figure something out and one more for Dean to begin to get his strength back. Benny gave most of his meals to Dean and made sure he tended to all the wounds inflicted upon his best friend when he came back from the monster’s torture.

But one fateful day, Benny was able to seduce one of the female guards and get her keys. They got out, finally. They were free.

Dean and Benny made their way back to Dean’s home, doing what they could for food and shelter. And when they got there, Dean sneaked into his house and woke Sam, who started crying with how happy he was that he could see Dean again. He was so young when Dean was sold, but no matter what happened, he wasn't able to forget Dean's face or what his brother meant to him.

The brothers stole their father’s fortune and bought their own ship with Benny, finding people to join their crew.

It took years for Dean to be able to truly trust his shipmates with his life, let alone to be intimate with someone again. Benny, Sam, Charlie, and later, Gilda and Jo, were Dean’s only confidants. And they did everything they could to help him through his trauma.

 

Dean stopped crying and looked at Benny, “You know.” He wiped away his tears. “You know better than anyone.”

Benny nodded, feeling a few of his own tears fall. “I do.”

“I couldn’t let it happen to him.”

“I understand,” Benny said and took one of Dean’s hands in his own. “It’s okay.” Dean sobbed again, gripping Benny’s hand. “Mates,” Benny whispered after a few minutes. Charlie and Sam left after giving Dean hugs.

 

Benny considered himself lucky. He wasn’t abused in the way Dean was; nowhere near as awful as Dean. Of course, Benny was scarred - both physically and metaphorically - and he needed time to recover as well, but Benny wasn’t a virgin, or as young as Dean had been, when he was taken and violated.

The day that Benny arrived at the abomination's castle is ingrained in his memories forever.

~

_January 24, 1673_

 

_“Oh, to-o-oy!” The creature sang while walking joyously in front of the two men dragging a beaten up seventeen-year-old Benny. “I have a surprise for you!”_

_Benny heard whimpers of distress and when the cell was opened and he was thrown in he saw the source. At the time, Benny didn’t know the boy’s name, but he was obviously malnourished and sickly._

_The then fifteen-year-old-Dean couldn’t help himself from breaking down and sobbing so hard he couldn’t breathe when he saw Benny._

_“Ah, what a_ stunning _sight,” The monster cooed at Dean, raking his eyes over the wailing form of what once used to be a person with hopes and dreams. “Unfortunately I have somewhere I need to be.”_

 _The broken boy pressed himself against the wall and shook his head. “Stop!_ Please _!” He lamented._

 _The creature threw his head back and growled in frustration. “_ God _!” He shook his head and looked back at the small, ill form with evil, lust-crazed eyes. “I’m going to have_ so much _fun with you later. I have something…” The monster’s eyes glinted evilly, “Special planned for today.”_

_Dean was crying so hard he couldn’t raise his voice above an utterly crushed whisper, “No!”_

_The monster slammed the cell closed, pressing himself up against the bars. “It’s been seven years, Dean. Happy anniversary.” He beat his fists against the bars and he left, whooping and yelling his way through the sub-dungeon. Dean flinched with every echoed noise. Benny could practically feel Dean’s hopelessness and despair from across the cell._

_“I’m sorry.” Benny heard the broken sob. “It’s my fault you’re here. I’m so sorry.”_

_Right then and there, Benny knew… He knew this boy was broken. Broken beyond anything Benny alone could fix._

_“Dean,” Benny said, testing his own hoarse voice. “This is not your fault.”_

_“It is,” Dean protested, “I asked him to do it to someone else. Anyone but me. It’s my fault you’re here.”_

_“Dean,” Benny got up and walked over to Dean, sitting in front of him. “Listen to me and listen closely: this is not your fault. That disgusting piece of shit-scum is to blame for this. He didn’t… He didn’t have to take me. And he did not need to kidnap you-”_

_“He didn’t.”_

_“What?”_

_“He didn’t kidnap me. He bought me,” Dean bawled. “My father sold me.” Benny was aghast._

“Your…” Benny felt himself becoming sick. _“Your_ father... Sold _you to this man?”_

_Dean dug the heels of his palms into his eyes, “Yes.”_

_“Did he know what he was selling you into?!” Benny was almost to the point of yelling. He saw Dean nod his head yes. It was then that the older boy started crying as well._

_“He knew,” Dean held in a sob, “Alastair told my dad exactly what he wanted me for, and my father named a price. Alastair paid and I was his.”_

_“I’m so sorry, Dean.” Benny reached his hand out to Dean. “I’m_ so _sorry.” Dean cried harder again and launched himself into Benny’s arms. “Well, I’m here now, Dean. I’ll be taken in your place.” Benny rubbed Dean’s back. He felt him shake his head and sob violently._

 _“No, he won’t. He only wants_ me _. He just brought you here to torture me,” Dean let out a gut wrenching sob. “I’m so sorry!”_

_Benny didn’t know what to do and he just held Dean until the kid fell asleep. He held him until Alastair and his men came back for Dean. Benny threatened them to stay away. But he couldn’t help Dean. The men beat him and took Dean. Benny had to spend the night in their cell sobbing and screaming to take himself in Dean’s place while listening to the boy’s screams of unbelievable torment and anguish._

_It was almost too much for Benny. But he knew he had to help Dean. He had to get them out…_

_And he promised himself right then and there: No matter what it took... He was going to make Alastair_ suffer _._

~

“Hey,” Benny comforted, getting onto his knees to pull Dean into a hug. “It’s okay.”

“I’m sorry,” Dean sobbed just like he had when they first met.

“It’s not your fault, Dean,” Benny comforted, rubbing Dean’s back. He traced the scar along Dean’s spine, making Dean jerk away slightly; but the older man kept Dean pressed against his body firmly. “It was never your fault.”

 

Benny remembered how hard it was for Dean to come back from his abuse. Charlie, Sam, and he did everything they could to help him. They would all admit, it was hard. Considering how much of a people pleaser he was; always wanting them not to worry about him and saying he was fine, especially for Sam.

But he knew when Dean was lying. He’d been to the sub-dungeons of Castle Purgatory with Dean; he was incapable of lying to Benny.

And since Benny and Dean had been in Alastair’s clutches together, the older man knew he had to do something to push Dean to get better.

~

_July 19, 1679_

 

 _“You want_ what?!” _Dean asked, his voice going up in pitch._

_“Look,” Benny started, walking over to the taller man, “You’re not getting better.”_

_“Benny,” Dean hissed, “I’m fine.”_

_“No! You’re not!” Benny yelled. He reached out and grabbed Dean’s hand. “I want you to have sex.”_

_Dean shook his head. “No. I don’t want to.” He tried to move past Benny, but was blocked. Dean quickly walked back, away from his best friend and eyed him warily._

_“With me, Dean,” Benny took a step closer. “You know you can trust me.”_

_Dean looked at him with frightened eyes, “What about Andrea?”_

_“I talked with her about this, she think’s it could really help you.”_

_The Captain laughed nervously, looking anywhere but Benny, “I don’t think so.”_

_“Please,” Benny said in a low voice. “We’re friends, Dean. I’m the only friend who knows what you went through. I’m the only friend who experienced at least a fraction of what you did.”_

_Dean’s breathing sped up, his eyes became terrified, and his voice came out shaky beyond belief. “I don’t want to be fucked.”_

_Benny walked slowly over to Dean. “I don’t want to fuck you,” He said, reaching Dean and running his hand through the man’s hair. “Everything that happens is up to you. If needs be, you can hold my hands down where you can see them so you don’t even have to worry about me touching you. Not until you’re ready.” Dean’s shoulders started to droop as Benny leaned in to towards Dean’s lips. “I won’t do anything you don’t want me to.”_

_“I don’t want anything in me,” Dean said, jerking away from Benny. “I will not let_ anyone _do that to me.”_

_“You can be on top,” Benny said, pulling Dean back and tilting his head, offering his lips to Dean. He waited for Dean to initiate anything, knowing if he wanted Dean to be able to go through with this, he’d have to have Dean be the one to start it._

_Finally, Dean breathed in through his nose and pressed his lips hesitantly to Benny’s for a few seconds before pulling away. He hovered over Benny’s, trying to decide if he wanted to kiss again. Dean placed his hands on Benny’s hips, slowly. Unsure if he could continue anymore. Dean whispered, scared and fingers shaking, “I don’t know if I can do this.”_

_“We can take our time,” Benny reassured him, “We don’t have to do everything in one night.”_

_“O-okay,” Dean stuttered._

_“Is it okay if I touch you?” Benny asked. Dean gripped onto Benny’s hips, forcing himself to nod. Benny moved his hands and gently laid them on Dean’s shoulders. “How are you doing?” Dean leaned forward and kissed Benny again, moving his lips more confidently against the shorter man’s. But something was wrong. Benny felt wetness against his cheeks and pulled back. Dean was crying._

_Benny immediately removed his hands from Dean. “Hey,” he said quietly, trying to get his friend to look at him._

_Dean gripped Benny’s hips tightly once more, most likely creating some bruises where they were, before letting go and letting out a sob. “I’m scared, Benny. I’m really scared.” He moved and hugged his best friend, shoving his face into Benny’s shoulder._

_“I know, Dean, I know. I’m going to touch you.” Benny used one of his arms to rub Dean’s back and the other to run through his hair. “I was scared, too. But sex isn’t bad. Andrea showed me that. It’s not about hate; it’s about love.” Dean’s shoulders shook. “It’s about love. And I love you, Dean. You’re my best friend.”_

_Benny could feel Dean’s sobs through his bones. It broke his heart to hear his friend so distraught, but he knew it was for Dean’s own sanity and recovery._

_Dean and Benny took weeks to finally get into bed together. Benny never touched Dean without asking, and Dean made sure to never hurt Benny._

 

_Dean was able to get through his fear with Benny by his side every step of the way. The first night he and Benny slept together had Dean sleeping until noon the next day - eight hours past his usual wake up time. Benny took care of everything in his absence._

_Dean asked Benny to have sex with him a few times after that, not ready to bare himself to someone else in that way. But Dean never abused the kindness his friend gave him._

_Months after Dean and Benny had stopped, Jo came on board, she and Dean had an instant connection; a year after Jo’s first step on board, Dean worked up the courage and told her what had happened to him. She cried for him and handled him delicately. They had tried to make love one night, but afterwards they felt something was lacking; because of that they stayed friends._

_To the credit of his friends and family, Dean was able to move past his utter self-hate and get to a point where he was able to cope with what had happened to him._

~  ~  ~

Cas woke up in his bed, with an ice pack on the side of his head where his father had hit him. He pushed himself up into a sitting position, wincing at the pain in his head. There was a note on his bed stand from his uncle:

“ _Cas ~_

_I came over to find you on the kitchen floor so I tucked you into bed. I’m sorry for how Michael treats you. I wish there was more I could do, but no one believes me. Just know that I’m here for you whenever you need it. I love you._

_~ Gabe._ ”

Cas set the note back down before checking the time. Seven fifty six. He immediately brightened up know that Dean should be here rather soon so he walked out onto his balcony and waited. The fresh air helped to clear his head and ease some of the pain he felt.

He didn’t see any sign of him, though. Not for at least half an hour. He began to think that Dean had changed his mind and wasn’t going to come see him. But then he saw a quick movement in the shadows next to the ivy covered stone wall separating Castiel’s yard from his neighbors.

The next thing he was was a man leaping from the wall onto the vine-covered trellis bolted against the back of his house, gracefully making his way up to Cas’s room.

“Dean?” Cas whispered. The pirate looked up and smiled, climbing faster and then pulling himself over the ledge.

“Hey, Cas,” Dean said, his voice barely above a whisper. Cas immediately wrapped his arms around Dean’s neck and pulled him into a kiss, only breaking because Dean needed to catch his breath.

“I didn’t think you were coming,” Cas whispered, moving to kiss at Dean’s neck.

“I always keep my promise,” Dean said, pulling Cas against him. The taller man grunted when Cas started to suck on Dean’s neck with no real pattern to where he put his lips. Dean ate it up, though. He made quiet, low noises that persuaded Cas to continue.

Cas was getting so into he almost didn’t notice when he felt Dean’s length push into his thigh. It made him smile to know that he could do that to Dean. Cas reached his hand down and felt Dean, making the taller man grunt again before pulling him into the dark of Cas’s bedroom.

“Someone could see us out there,” He said breathlessly, backing up to Cas’s bed.

Cas nodded and pushed Dean onto his bed, fingering over the buttons at the waistline of Dean’s pants. “May I?” Cas asked, Dean smiled and sat up.

“Not tonight,” He said, putting his hands on Cas’s waist and pulling him closer. Dean’s face was level with Cas’s stomach.

Cas frowned, “Why not?” He asked. Dean let out a small chuckle and rest his forehead against the boy’s stomach.

“I have a feeling you’re still sore from last night. And believe it or not, but I’m sore, too.” Dean looked back up at him. “Plus, I’d like to get to know you better.”

Cas felt himself smile. He laced his fingers into Dean’s hair and nodded. “I’d like to get to know you better, too.”

Dean smiled and let go of Cas, scooting up on his bed. Cas came and sat down next to him, but Dean pulled him into his lap, legs on either side of Dean’s hips.

“What do you want to know about me?” Dean asked, rubbing the top of Cas’s thighs endearingly.

Cas smiled wider, placing his hands on Dean’s shoulders. “What’s it like being a pirate? What do people do on board? What jobs are there?”

Dean took a breath. “Well, being a pirate… It’s hard, I won’t lie. But it’s also so freeing to be able to do as you please when you please. You get to make the rules and you get to break them. I love my ship, the Impala 67. She’s my baby. And I love my crew. They’re some of the best and most honest men and women you’ll ever meet.

“Benny’s my barbecue and he can cook like nobody’s business. His pie is to die for. Charlie, she’s the Quarter Master and she does a _fantastic_ job. She’s honestly one of my closest friends and she’s great at making sure I know what my crew needs and when they need it. Then Sam, he’s my Sailing Master, he maps out the course we’ll be taking when we set out. Ash, you met him, he’s weapons master. He’s one of the smartest men you’ll ever meet.

“Gilda - Charlie’s wife, she’s our medic. Boy, can she patch you up. I once had a cut on my arm so deep I almost died from blood loss, but she got in there and just stopped it. I mean, she’s got an unfair advantage. She’s got magic in her veins. Then there’s Kevin, my boatswain and carpenter. And Jo, my Master Gunner - she’s amazing at aiming the cannons.

“Lastly we’ve got the mates, able bodied sailors, riggers, cabin boys, powder monkeys, and then the swabs. They’re the backbone of a ship, to be square. What I do is just over glorified decision making.” Dean finished, looking in love with everyone he’d listed off. He looked back at Cas, still smiling. “We’re a family.”

Cas could feel himself beginning to frown. That’s not something he’d ever had. “What’s that like?”

“What’s what like?” Dean asked, “Having a family?” Cas nodded. Dean frowned and searched his eyes; Cas felt as though his soul was being examined. “I didn’t always have a family, either,” Dean whispered, not breaking eye contact. “I know how hard it is to feel alone; like you’ve got no one. I’m sorry, Cas.”

Cas shook his head. “I have my uncle, Gabe. He’s really the only family I have.”

“No brother’s or sisters?”

“I’m an only child.” Cas leaned into Dean and put his head on his shoulder.

Neither one of them spoke for a long while. Once again, comforting each other.

“What’s your favorite color?” Dean asked, breaking the silence. Cas closed his eyes.

“Green,” He said. “Like your eyes.”

Dean chuckled, “Really?”

“It used to be yellow like bees, but once I saw your eyes it changed,” Cas said shyly, “It’s a beautiful color.”

“Thank you,” Dean responded, leaning his head against Cas’s.

“What about yours?” Cas asked.

“Blue.”  

“Like my eyes?” Cas smiled.

Dean laughed and nodded. “Yeah, I didn’t have a name for it until now.”

“What name?”

_"Royal Cas.”_

Cas felt a laugh bubble up in his throat. “I like it.”

Dean laughed, as well; he moved his arms around to encircle Cas. “Thank you.”

They spent the night like that: in each other’s arms talking, laughing quietly, and sharing stories. When their eyes started to close on their own, they got under the covers and cuddled.

Both of them tried to stay awake as long as possible, not wanting to miss a moment with the other, but found themselves asleep within minutes of each other.


	3. Chapter Three

**Summary for the Chapter:**

> Dean's been docked for three weeks. His ship is all stocked up and fixed. The Impala's crew are itching to get going again. 
> 
> What about Cas, though?

Chapter Three

_September 29, 1692_

 

Cas and Dean went on seeing each other whenever they could for the weeks in which Dean was in port. But they both knew it would come to an end; sooner than they would like. By the third week, they became desperate for each other.

They couldn’t see each other during the day. Dean had his ship and crew to tend to, and Cas had his father’s meetings and schooling. That only left the nights for them to be together.

It took some time for Dean to agree to have sex again. He didn’t want their time together to be based solely on that act. He wanted to get to know Cas, find out who the boy he was so taken with was as a person before a lover, despite the circumstances in which they met.

Currently, Cas was sneaking out of his house. It was around midnight, the time in which he knew his mother and father were in deep sleep. He could feel himself starting to breathe hard in anticipation for what was to come. Dean seemed to know all the best places to make Cas writhe with pleasure.

He was headed there now, sprinting through the streets and keeping his face hidden. Cas found out that Dean craved his touch just as much as he craved Dean’s. It made Cas feel important and special that he was the one the Pirate King wanted.

Dean offered to come to Cas at his house, but they decided it was too dangerous. Plus, Cas liked when Dean walked him home the long way early the next morning. He liked how Dean would hold his hand and they would walk together along the shore and into the woods. In the mornings they were away from prying eyes and were allowed to enjoy each other’s company.

Right now, though, Cas was slowing down to catch his breath before meeting up with Dean. He was hiding in one of the alleys while doing so just in case there were any stragglers still out at this time.

When he caught his breath enough and checked for any signs of people, he jogged out to the docks.

“Dean!” He called, smiling and breaking back into a run. Dean turned and caught Cas in his arms just in time. They kissed deeply before Cas was put down. “Are you ready?” Cas teased, backing up the stairs that would get them onto the Impala. Dean raised his eyebrow and the corner of his mouth twitched up.

“Are you?” He asked, starting to follow Cas up the stairs. Cas’s smile turned into a devious grin as he spun around and sprinted up the stairs, not even hesitating when it came to jumping onto one of the ropes to swing onto the deck of Dean’s ship.

Cas heard Dean’s heavy footsteps following him to his cabin. He didn’t need Dean to lead him anywhere on his ship anymore, he’d memorized the layout one night while Dean was busy with a project her and Ash were working on. When he told Dean about it, Dean had said he found Cas’s studiousness cute.

Dean kept his eyes on his lover as Cas flung open the door that led to the hallway with the Captain’s cabin at the end and dashed inside; he was close behind the boy.

When Dean caught Cas just outside the door to his cabin, the boy squealed and laughed loudly. Dean picked him up and carried him into the bedroom, tossing him down onto the bed and climbing between his legs.

They kissed desperately and all but tore each other’s clothes off, throwing the articles in various directions.

“I’ve been thinking about you all day,” Cas said between kisses, “Wanted you so bad.”

Dean chuckled and moved himself down to be level with Cas’s groin, taking no time to hollow his cheeks and flatten his tongue against the underside of Cas’s member. He bobbed his head quickly and pushed Cas's legs father apart before pulling off of his shaft for just a second to suck his finger into his mouth. Cas watched him with wide eyes and a flushed face. Dean smiled and took the boy's cock back into his mouth as he circled Cas's entrance with his finger.

Cas moaned loudly and laced his fingers in Dean’s hair. The pirate moved his head along the length at an increasing pace, loving the noises Cas was making. When the pirate started to hum around Cas, the boy surged up on the bed into a sitting position and bucked his hips violently, coming in Dean’s mouth with a shout.

“I’m sorry!” He said immediately after. Dean pushed himself back up to be eye level with Cas. The boy looked mortified. He may be new to sex and pleasure, but he usually didn't come that quick.

Dean only smiled, some of Cas’s cum on his bottom lip. “Don’t even worry about it,” He reassured Cas.

“I didn’t… I didn’t…” he lowered his voice to say the next part, blushing profusely. “...Choke you... Or anything?” Cas asked.

Shaking his head, Dean licked off the white line of Cas’s cum from his lip. “Not at all. In fact,” he sucked his bottom lip into his mouth, “I quite liked it.” Dean leaned forward, hovering over Cas’s own lips. “Do you want to taste?” Cas felt himself nodding before he was pushed back down onto the pillows and his mouth was attacked by Dean’s. The older man’s tongue was in his mouth and Cas moaned when he tasted the hints of something just a bit salty, but also rather sweet. It wasn’t entirely unpleasant.

Dean pulled away, “Do you like how you taste?” He asked, smirking.

Cas nodded. “Do _you_ like how I taste?” He asked shyly, fidgeting with the covers beneath him.

“I don’t,” Dean said. Cas felt his stomach drop until Dean leaned down and almost moaned into his ear, “I _love_ it.”

Cas shivered and fisted his hands into the sheets. “Are you-” his breath caught in his throat as Dean bit down on his ear lobe lightly. “Are you sure I didn’t choke you?”

“You’re too small, angel,” Dean said as he trailed ghost kisses down to Cas’s neck. He had often said how much he loved how small Cas’s cock was. ‘ _It fits in my hand and mouth so perfectly,_ ’ he said one night while Cas was trying to control his breathing and come down from the high of his orgasm. Which gave Cas butterflies and make him love being with Dean that much more.

Cas stuttered, “I-I wanna taste you.” Dean let out a shaky breath.

“You can’t do that to me, baby,” He said, gripping Cas’s hips and rolling them over so Cas was straddling his lap. “You gotta warn me before you do something that bloody hot.”

“Sorry,” Cas said, totally not meaning it. “Lie down.”

“Love it when you boss me around,” Dean flirted, letting himself be pushed down by Cas to rest his head on the pillows. He grabbed Cas’s hand before the boy could move down. “Don’t try and take me all in like I do with you.”

Cas nodded, “I won’t.” He pecked Dean and then kissed his way down the man’s broad chest.

“Use your hands for most of it,” Dean said, pushing himself onto his elbows. “How about-” Cas shushed him. Usually he found Dean’s concern with his well being very pleasant, but right now he was being a nuisance.

“Dean, I’ve got you.”

Dean nodded, “Okay.” He didn’t fall back onto the pillows, and instead watched Cas place open mouthed kisses along his length, starting from the base and working his way up. Cas knew Dean was a rather quiet partner in bed. He didn’t scream or cry out like Cas did. But the noises he did make made Cas lose his mind. He loved being able to hear when Dean liked something he did.

When Cas got to the head of Dean’s cock, he took it into his mouth, wrapping his hands around the rest of Dean’s shaft. A long low groan was drawn from Dean’s lips, giving Cas even more incentive to keep going.

He followed by example and sucked at Dean’s head while twisting and pumping his hands around what he couldn’t fit in his mouth. Cas looked up at Dean from where he was to see the man watching him with lust-blown eyes. There was something else in them… something more tender and soft…

Cas wasn’t willing to go into it right now, though.

“Fuck, Cas,” Dean moaned, his eyes lolling back into his head for a minute before he could focus on Cas again, smiling. “You sure this is the first time you’ve blown a guy before?” He joked.

Cas laughed around Dean, making the older man’s eyes screw shut and a sharp inhale of breath to be very audibly heard. After that Dean’s breathing became intensely haggard and uneven.

“Fuck!” Dean cursed, his head falling back as his breaths turned into shallow pants. “Gods, Cas! I’m gonna come.”

Cas flicked his tongue across Dean’s slit before pulling off to speak, not stopping his hands. “Then come.” As soon as he finished he was taking Dean back in his mouth and sucking more violently while swirling his tongue around wildly.

“Fuck!” Dean almost yelled, falling back onto the pillows and coming. Cas slowed down, moaning at the taste of Dean’s cum. He wasn’t able to describe it, if he was being honest… The only thing that could come to his mind was that Dean was… Well, _Dean_. Cas noted it was very different from how he tasted. He also noted that he liked Dean’s cum more than his own.

“You taste amazing,” Cas said, gingerly sucking Dean’s tip trying to get every drop of cum out of him.

“I taste amazing?” Dean asked, his breathing still uneven. He twitched and his hand found Cas's hair, telling Cas he needed to stop. Cas let go of the man's softening cock and ran his hands over Dean's stomach, admiring how muscled he was. 

Cas nodded, “Even more than amazing.” The older man smiled. Cas slid off from straddling Dean and came up to lay next to him. Dean turned his head and kissed Cas, pushing his tongue into the boy’s mouth.

“Apparently, I do,” Dean noted, “All I get from you is _you_.”

Cas blushed, kissing Dean again. “How much time do you need?” He asked, pushing his face into Dean’s neck.

“Not too long,” Dean responded, tilting his head to lean on Cas’s. “What about you?”

Cas answered by pushing his already hardening cock into Dean’s side. “Less time than you.”

Dean chuckled, rolling back on top of Cas. “We’ll see about that.” He leaned over Cas to grab the oil they usually used from his nightstand. “Stomach?”

Cas nodded and quickly flipped himself over onto his hands and knees, looking back to watch Dean dip his fingers into the oil and coat them thoroughly. When he caught Dean’s eye, he let himself be pushed into the mattress.

“Ready?”

“Dean, _yes_ , just _touch me_ ,” Cas gasped, a little annoyed that Dean felt he even needed to ask. He closed his eyes in anticipation and mewled when he felt Dean’s oiled finger push into him. “More!” He pushed back onto Dean’s finger.

“Sh, angel, calm down,” Dean rubbed Cas’s back tenderly as he gingerly added a second finger, making a big show of searching for the spot that made Cas lose it.

The boy could feel tears start to form in his eyes from need. “Dean,” he almost cried. “Please!”

Dean awarded him with another oiled finger, all brushing against his prostate. He launched himself up off the bed and into Dean’s chest, scrabbling to find purchase in Dean’s hair. Dean stopped moving his hand and let Cas fuck himself on his fingers, smiling and licking over the boy's neck.

“Are you about to come again?” Dean asked, his breath heated in Cas’s ear.

“No,” Cas didn’t outright lie. He wasn’t _about_ to come, but he was close to feeling the heat pool in his abdomen.

“You want me to fuck you?” Dean growled.

“Yes, please!” He bit his lip, tasting salty tears on it. Dean pulled his fingers out and held onto the boy’s hips, rubbing circles into his hip bones as Cas thrust into the air.

“Do you want to ride me again?” Dean asked, much softer now. He kissed along the nape of Cas’s neck, still rubbing soothing circles into Cas’s hipbones.

Cas bit his lip in thought before shaking his head. “No.”

“Are you sure?” Dean smiled. The last time Cas had tried to ride Dean he wasn’t able to because it was too overwhelming. He came as soon as he sunk down onto Dean’s cock and Dean had to finish himself off because Cas was too strung out. He felt awful, but Dean kept telling him it wasn’t a big deal.

“Yeah. Not just yet,” Cas shook his head.

Dean smiled wider, “Okay.” He swept Cas off the bed and gracefully laid him down on his back again. Dean made quick work of lubing his cock and then of lining himself up with Cas, only pushing the head of his cock in. Cas’s arms snaked themselves under Dean’s arms and then bent to encircle the man’s shoulders. Dean palmed Cas's thighs and brought them to lock around his hips, as well. 

In one swift movement, Dean bottomed out. He looked at Cas and smiled to himself. The boy’s eyes were closed and his mouth was hanging open.

“God, Cas. You look so perfect,” Dean cooed, feeling Cas’s fingers dig into his shoulder. Dean was busy memorizing Cas’s face, hearing huffed out breaths of arousal leave Cas’s lungs.

“Move!” He demanded with a whine, pitching his head forward to bite the crook of Dean’s neck; not enough to hurt, but enough for Dean to get the picture. Dean pulled out and thrust in, not being able to help the almost pathetic pant he let out. He set a slow pace until he felt Cas bite down harder on his shoulder. “Harder,” Cas gasped out, clinging to Dean.

“Fuck,” Dean moaned and pounded into Cas, making the boy cry out.

“Dean!” Cas lifted his head and caught Dean’s lips with his own, pushing his tongue into the man’s mouth. Dean met Cas’s tongue with his own and massaged it until he needed air.

Dean pulled away from Cas and leaned their foreheads together. “Wanna hear those beautiful noises you make.”

“Ah!” Cas gasped when Dean brushed against Cas’s prostate. “Right there!”

“If you say so,” Dean grunted out, angling his hips to hit the same spot as before. Cas’s eyes rolled back in his head and he dug his nails into Dean’s back almost hard enough to draw blood. It hurt Dean in just the right way, making him pound into Cas harder. He made sure to hit Cas’s prostate with every thrust.

Cas’s legs began to tremble around Dean’s waist and his arms let go of Dean to grab onto the headboard, his knuckles turning white from his grip.

Dean reached between them and started to jerk Cas off, whispering into the boy’s ear, “Feel good? You like when I have my hand on your cock and my dick inside you.”

“Yes!” Cas screamed, loud enough to wake up the whole ship if they were anywhere else.

“Show me how good it feels,” Dean said. He gripped Cas’s cock in his hand tighter and thrust his hips just a bit harder and deeper.

Cas arched his back violently into Dean’s chest and screamed, “Dean!” Cum coated his stomach and Dean’s hand in thick white stripes. Dean wasn’t far behind; with Cas being so tight and the noises he made when they were in bed together, it was hard for Dean to be able to control himself. He lifted his hand up and licked away the lines of white staining his fingers, moaning with how absolutely amazing Cas was. He groaned Cas’s name, hints of the boy’s cum still on his tongue, before he filled Cas up with his own cum.

“Fuck, you’re so beautiful.” He slumped down onto Cas, continuing to thrust shallowly as he rode out the final waves of his orgasm.

“Hey,” Cas said, his voice quiet. “Dean, up.” Dean smiled and pulled out of Cas as he pushed himself up onto his arms.

“Sorry,” He panted and kissed Cas’s neck. Both boys couldn’t move, nor did they want to. 

“Dean,” Cas tugged at Dean’s hair. “Towel?” Dean nodded and rolled off of the boy, making to grab a damp towel. He was stopped short when coming back to see the fucked out boy with his eyes closed and panting Dean’s name quietly like it was the only word he knew.

Dean was sure that if he were going to die anytime soon, this boy would be the cause. “You’re killing me, Cas.” He sat back on the bed and used the towel to wipe away the drying cum from Cas’s stomach and chest. He heard Cas whimper when the towel brushed against the tip of his spent cock and a small amount of cum to spill out. Dean used his thumb to wipe it up and then he licked it clean.

“I’m… Sleep...” Cas trailed off, not being able to get any more words out before he fell asleep. Dean watched his face relax and his mouth open slightly. He started snoring, again. It made Dean smile and cup the beautiful boy’s face.

Dean didn’t realize he was crying until tears started falling on Cas’s stomach. He didn’t want to leave Cas. The time he’d spent with him was some of the best days of his life. And watching him sleep now, he felt himself wish - for the first time since he’d bought his boat and started this life - that he wasn’t a pirate.

This was a dangerous trap Dean was falling into here - and falling fast. One he wasn’t sure he’d be able to get out of... And one he wasn’t sure he really wanted too.

~  ~  ~

_September 30, 1629_

 

“Cas, baby, wake up,” Dean’s gruff morning voice pulled Cas out of his sleep. He felt Dean’s warmth behind him; the strength and the power the man held.

“I don’t wanna,” He mumbled, grabbing Dean’s hand and pulling it up to his mouth to kiss it. “Warm.”

Dean pulled Cas tighter into him, kissing the back of his neck. “Me too, but we gotta get you back.”

Cas whined and pouted, “No, my bed isn’t warm enough.”

“Baby,” Dean sighed, “We’ll see each other again tonight. I promise.”

“But I wanna spend the day with you,” Cas complained more. “I don’t wanna go back to my father. He’s _rude_.” Dean let out a shaky breath. In Cas’s sleepy state he was able to convince himself that he didn’t hear any tears in his lovers voice when Dean spoke.

“I’m sorry. I know, I don’t want you to leave either. But, c’mon. We have to.”

Cas felt Dean start to leave, making him whine and turn to grab out at him. “Dean, _no_!” The man’s lips were placed softly against his. Cas responded immediately, trying to deepen the kiss, but Dean kept it sweet and loving. It took Cas’s breath away.

“C’mon, you’re awake now,” Dean said, breaking the kiss and wrapping his arms around the still sleepy form of Cas, dragging him out of the warmth of the bed, but not letting go of him.

Cas leaned back into Dean, “I want to sleep with you forever.”

Dean chuckled and set Cas on his feet. “Me too, babe. We can do that tonight.” He made sure Cas wasn’t going to fall as he walked around his bed to his dresser to grab an extra pair of Cas’s clothes he’d brought one night, just in case.

“I like when you call me names like that,” Cas said, rubbing the sleep from his eyes. “Angel, baby, babe… All of them.”

“Okay dopey, get some clothes on,” Dean tossed the outfit to Cas, “Not that I don’t like the view.” He looked at Cas’s naked form and felt himself yearning to touch every part of him; to kiss away all the boy’s worries of the future, to smooth away the hurt of the present, and to hold him so the sadness of the past melted away.

Cas finally reached his hands up and stretched. “Okay,” he yawned, blinking slowly and beginning to get dressed. “I’m going.”

Dean followed suit and within ten minutes, the two were walking above deck and jumping onto the wood docks to get Cas home, holding hands and keeping each other warm in the chilly August morning air.

~  ~  ~

Later that night, Cas snuck out and ran to see Dean again. But something was wrong, Dean was hesitant to get onto the Impala just yet.

“What’s wrong?” Cas asked, keeping his eyes on Dean’s face.

“It’s been three weeks,” Dean stated.

“Yeah?”

“I have to go,” he couldn’t look in Cas’s eyes.

“What?” Cas was dumbstruck. “You’re leaving?”

Dean looked at him desperately, “My ship is fixed and we’re all stocked up for the next few months out at sea.”

“You’re _leaving_ me?” Cas could feel himself starting to cry. “Dean, I…”

“Nay, Cas, I would never leave you,” Dean took Cas’s hands in his own.

“But you’re going back out to sea!” Cas yanked his hands away, feeling like his chest was about to collapse.

“Cas,” Dean’s voice was desperate and watery, “I don’t want to go. But I have to.”

“So you’re just going to leave me here?” Cas cried angrily, “You’re going to abandon me?!”

“No!” Dean was crying now, too. “I would never leave you like that; I’ve talked with my crew about this. They-They have all agreed we’ll come back to Heaven to fix the ship and restock.”

Cas felt his chest constricting, “You’re leaving me alone.”

“I’m so sorry, Cas,” Dean pleaded with him. He kept bringing his hands up to his face to wipe away his tears. “I’m so sorry. _Please_ , understand, I can’t abandon my ship or my crew. I have responsibilities and I have contracts to deal out and collect. I don’t _want_ to leave you…”

Cas stood there watching Dean angrily. Neither of them spoke. Not until Cas got an idea that had his anger melting away and being replaced with an overwhelming feeling of need. He rushed over and took Dean’s face between his hands. “Take me with you.”

“What?! Cas, nay, it too dangerous,” Dean was shaking his head almost violently. “The storms and the other pirates. I care about you too much to put you in that kind of danger.” Cas felt his anger return. He pushed Dean back harshly, making a sob leave the taller man’s throat.

“Then why are _you_ out there!?” Cas felt more tears slide down his cheeks, his anger falling away with them fast. He fell to his knees. Dean's arms came around him in an instant as he started hyperventilating. “Dean… I… I can’t stand the idea of losing you.”

“Angel, I promise, I’ll come back.”

Cas sobbed and clung to Dean, “But what if you’re killed?”

Dean hugged Cas even tighter, “Not gonna happen. I’m invincible.”

They stayed together for what seemed like hours, but Cas knew it was most likely only seconds before he urgently took Dean’s shirt in his hands and kissed him desperately, their teeth crashing together and lips being bitten and pinched in their wanton need. “Dean…” Cas gasped out against Dean’s lips. “Make love to me?”

“Cas,” Dean breathed out, picking the boy up. Cas wrap his legs around Dean’s hips and somehow they managed to get into Dean’s cabin and then under the covers of Dean’s bed.

They made love slow and desperately, clinging to each other and touching as much skin as possible. Neither of them wanting to let go of the other even for a second; both crying because of the pleasure and the fact they wouldn’t be able to see each other for months.

It would be hell for both of them.

That night, neither fell asleep. They didn’t dare miss one second with the other.

 

When it was early in the morning, around three AM, when the sun still wasn’t up, Dean walked Cas to the edge of the docks. They kissed each other with so much emotion it left them both with unshed tears in their eyes.

“Cas,” Dean panted, his forehead against Cas’s, “Take this.” He handed Cas a small sack.

“What is it?” Cas asked.

“Oil and a few other things you can use if you start missing me,” The pirate answered. “I had a plug made for you, too.”

Cas looked around and blushed, “A plug?”

Dean smirked, sadness still tugging the corners of his mouth downwards, “To keep yourself ready for my return.”

“Oh,” Cas whispered, clutching the burlap tightly. “Thank you, Dean.” They were silent for a while, keeping their foreheads pressed together and nuzzling their noses together.

“I’m going to miss you, Cas,” Dean whispered, “So much.”

“I’m going to miss you too,” Cas whispered back, pressing a kiss to Dean’s lips. “Don’t forget about me when you’re out there... Bedding others in my absence.”

Dean shook his head, “Nay. I’m not taking anyone else to my bed.”

Cas felt himself crying. “Come back soon,” he said, giving Dean one last kiss before pushing him away.

Dean walked away sadly, his shoulders slumped and his footsteps heavy.

Cas watched the ship sail away long after it was gone, almost until the sun came up. When he got home he went straight for his bed and broke down, sobbing into his pillows.


	4. Chapter Four

**Summary for the Chapter:**

> Dean's absence is hard on Cas. He finds himself worrying if he'll ever see the pirate again; seeing as being a pirate is not an easy profession and it comes with a price if done wrong. 
> 
> It's coming up on six months of Dean being gone; the maximum amount of time Dean promised he'd be gone. Cas is starting to really worry. 
> 
> What if Dean isn't coming back?

Chapter Four

_February 13, 1693_

 

The months in which Dean was at sea was torture. Cas sunk into a deep depression. His uncle served as his only confidant and the only thing keeping him from never leaving his room... Most of the time. They were in there now.

“How many months has it been now?” Gabe asked, helping Cas make his bed.

“Four,” Cas answered, frowning.

“How long did he say he was going to be gone for?”

Cas looked up with a pained expression. “He said he’s never at sea for less than three months.” He took a shaky breath to calm himself down. “But he promised me no more than six.”

“I’m sorry, Cas,” his uncle consoled him, laying down on his newly made bed. “Worst comes to worst you’ll only have to wait another two months.”

“If worst comes to worst then I won’t see him ever again.”

“Castiel,” Gabriel gave him a disapproving look, “If Dean “ _The Righteous Man_ ” Winchester was dead, we’d be hearing about it right now.”

The blue eyed boy shut his eyes and rubbed his temples before saying, “Why don’t we talk about something else?”

“Sure thing,” Gabriel looked around and his eyes landed on the bottle of oil Cas kept on the night stand next to his bed. In case Dean came back. “What’s that for?”

Cas looked up and blushed, hiding his face as he spoke, “Nothing.” 

“I get it.” Gabe looked at his nephew and smirked.

Cas was mortified. “Not this subject, please?”

“Oh alright,” Gabe got up and walked around Cas’s room.

“Can we go somewhere?” Cas asked, fidgeting with his hands. “I can’t be in here anymore.” He looked at the pillows on his bed longingly, remembering the night Dean and he spent talking after they'd first met.

“Let’s go to the Square,” Gabe suggested, walking over to Cas and throwing his arm around his nephews shoulders despite being at least a head shorter than Cas.

“Let’s go,” Cas nodded and let his uncle lead him to out of his room and then his father’s house. They walked close together and Cas let Gabe do all the talking, letting his own mind mull over whatever it desired.

He found himself thinking about when he told his uncle about Dean. Gabe had found him sobbing on his bed a month or so after Dean had left and Cas told him.

 

_“Castiel,” Gabe had started. His eyes were wide and Cas could see he was getting worked up. “Did you ever think that he was only using you because you’re Michael’s son?”_

_Cas shook his head, “That’s not what this was about.”_

_“How do you know, though?” Gabe was pacing at the foot of Cas’s bed._

_“Gabe, he-”_

_“Castiel! He’s a_ pirate _. Pirates_ lie _for a living!”_

_“After we first slept together,” Cas started, keeping his voice calm. He heard Gabe make a noise between a scoff and a snort. “He came and saw me the night after, too, and-”_

_“And he fucked you again.” Gabe stopped and turned to Cas, “He was using you! He_ is _using you!”_

_“No!” Cas lost his temper, “He didn’t. In fact, when I asked to go farther he said no; he wanted to just talk.”_

_Gabe seemed to be surprised. “That doesn’t mean that he wasn’t using you.”_

_“You’re not getting it Gabe,” Cas said, calming himself down. “He was ported for a little over three weeks. I met him on the first night he docked, and we slept together. We saw each other every night after that. But we didn’t have sex again until his last week docked.”_

_Gabe sighed, running his hands through his hair. “So, he’s a good actor.”_

_Cas felt himself shaking his head, “You’re wrong.”_

_“How do you know?”_

_“Whenever things started getting too heavy, he stopped us.” Cas blushed. He didn’t like talking about things so intimate with anyone; even if it was a little easier with Gabe. His uncle got him in a way no one else did. “Trust me, Gabe, he was… He was having trouble stopping. I... I did not make it easy. But he did stop.” Cas wasn’t able to look at Gabe for longer than a few seconds because of how flustered he was. "He stopped us no matter how much I said I wanted it."_

_“Castiel,” Gabe sighed, putting his hands over his face. “I’m worried for you. What if he’s just using you to get at Michael? I don’t want you to get your heart broken.”_

_“Please,” Cas forced himself to maintain eye contact. “Just trust me.”_

_Gabe put his hands on his hips and searched Cas’s face for a good couple of minutes before he spoke. “I trust you.” He threw his hands up. “I believe you. I’ll give you - and him - the benefit of the doubt.”_

_“Thank you,” Cas whispered, wiping his eyes from the tears he hadn’t noticed were falling._

_“But,” Gabe’s voice was sharp and cutting, “If he hurts you, I will kill him. I swear to God, I will kill him.”_

_Cas found himself laughing. “Thank you, Gabe.”_

_“I love you, Castiel,” Gabe smiled, coming to sit down next to him on the bed. “You know that. And you know I’d do anything I could to make your life easier.” He pulled Cas into his arms. “God knows I’ve tried.”_

_“I know,” Cas said, hugging his uncle. “I love you, too. Thank you.”_

 

“Castiel, are you in there?” Gabe pulled Cas out from his own head and back into the real world.

“Yeah, sorry, I was just thinking.”

“Well, stop. Just enjoy your time with me today,” Gabe smiled at him, clapping him on the back. “How about we get something to eat?”

“Sounds good,” Cas said, forcing a smile onto his face.

~  ~  ~

Cas spent the day with Gabe walking around town and visiting vendors along the street of Heaven. It wasn’t bad, though. Cas rather liked being able to think about something other than Dean and the emptiness he felt without him.

 _This isn’t healthy_ , Cas thought to himself. _I can’t let him take over my life._

It was hard, though. He didn’t know why, but it was as if his soul yearned for Dean’s. He wanted to be able to touch the pirate, kiss him, hug him, just _talk_ with him. 

And, Cas couldn’t outright deny he wanted to be intimate with Dean again. A smaller bolder part of him yearned to have Dean’s manhood in his hands or mouth, have Dean’s cum on his tongue; more than any of that he wanted to feel Dean moving inside of him. He wanted to be able to feel Dean’s want and need for Cas. More than even that, though, he just wanted Dean’s presence close to him…

Cas got up from his bed and walked over to the closet next to his door; that’s where he kept the presents Dean had given him. He pulled it out and swiped the container of oil off of his night stand — that was there in case Dean came back during the night so he wouldn’t have to grab it from his closet — and poured the contents out on the bed.

Dean had given him various toys to pleasure himself with. But he rarely used most of them save fort the ivory plug Dean had made especially for him and the hollowed out cylinder-shaped toy. It was smooth on the inside. Cas had found that he could pour some of the oil into it and then push it over his cock, either thrusting into it or using his hand to pump it over himself. Often times, he would open himself up with his oil-slicked fingers enough to push the plug in, and then thrust into the leather toy until he came. Other times he would just use the plug and his hand to jerk himself off.

Most of the time, after he came, he wasn’t able to clean himself up and would fall asleep with the plug still in. He didn’t mind the slight pain that came along with taking it out in the morning.

Tonight though, it was different for Cas. He found the plug before sweeping all the other toys back into the bag and dropping it to the floor. Cas didn’t want anything else except to feel like he was being filled up by Dean; even if the toy was too small to really be Dean.

Cas laid on his stomach and pushed himself onto his knees. He used his fingers to open himself up, muffling his already quiet whimpers and moans with his pillows. It felt so good for Cas to feel the burn of being stretched open, but it was nothing compared to when Dean did it.

His fingers were fine, yes, but they weren’t as thick or as long as Dean’s. And he found he couldn’t really get to the little bundle of nerves he so desperately wanted touched. But that didn’t stop him from trying his hardest.

After his release, he usually ended up having him laying on his bed, staring up at the ceiling with tears in his eyes from frustration. It was never as amazing as when Dean was behind him. The much bigger man's hand on his small cock or Dean's fingers in him. Cas missed the names and the praises he got from Dean.

He missed being called beautiful, angel, or baby. He missed the mornings after when he woke up with Dean spooning him or when he used Dean as a pillow. Waking up to the beat of his heart was Cas’s favorite way to wake up. It grounded him and reminded that there was someone who wanted to take care of him. It made him feel loved…

Cas found himself arching his back and moaning, “ _Dean!_ ” when he came that night. There was a wet spot on his pillow from his tears. He wanted his Dean back so badly. He wanted the man in his arms, and he wanted their chests pressed together.

It wasn’t about sex, for Cas. And he knew it wasn’t about sex for Dean either. The way Dean had to screw his eyes shut and curl his hands into fists to keep himself from ripping Cas’s clothes off and fucking him senseless those nights they spent together after their first was proof of that.

Cas stroked his cock through his orgasm, shoving his mouth into his pillow and moaning Dean’s name over and over again. He imagined it was Dean’s fingers that was in him right now. But, of course, it was hard because he couldn’t feel the man’s warmth or the usual soothing hand rubbing over his back.

He stopped when his cock became too sensitive and flipped over onto his back, his legs splaying open. He didn’t have the energy or the motivation to care about closing them or to slip under his covers. And he certainly did not have the drive to reach down and pull the plug out.

Cas did make sure the oil was placed back on the nightstand next to his bed along with a slip of paper with a note and Dean’s name next to it for on the off chance tonight was the night Dean came back.

Not even five minutes later, Cas was sleeping, not quite happy enough to be snoring.

~  ~  ~

“Sam!” Dean boomed from the quarterdeck where Kevin and Charlie were manning the helm. “How much longer?” He could practically hear his brother’s eye roll before he answered. He knew why Dean was so eager to dock at the ports of Heaven.

“Not much longer, Captain. Ten, fifteen minutes?” Sam didn't even look up from his station. Dean felt himself smile and his heart jump just thinking about Cas. After five and half months he was finally going to be able to see the boy he was so taken with again.

Kevin laughed. “Eager to see someone, are we?”

“Oh shut up, Kevin. You know the Captain’s got a boy-toy he loves.”

Dean turned to see Jo, walking up the step to the deck to help with the helm. “He’s not my boy-toy,” Dean shot back, knowing Jo was kidding, but not being able to help himself. “I like his company.”

“And his ass,” Jo added, winking.

“Well, that’s just an added perk... And _fuck_ if his ass ain't perky,” Dean smiled, laughing as Jo rolled her eyes and shook her head. He loved Jo like a sister. She was another one of the only people he trusted with his the secret of his past. 

“Ugh,” Kevin said as he heaved the helm to the left with Charlie’s help. The boat dipped slightly, sending some sailors off balance, but not Dean. His sea legs had become part of his personality. He was at home when he was sailing.

“Oi, why don’t you spend more time steering than worrying about my sex life, huh?” Dean put his hands on his hips and quickly jumped down onto the main deck. “Gather it up! We’re getting close!”

“Aye, Captain!” One of the swabs replied, scurrying around to disperse the message to the other’s. Dean walked across the main deck of his ship to the prow. He wanted to be able to see how close they were getting.

When he got there, he could feel his heart skip a beat and his stomach twist into a knot. Sam had exaggerated the time. They were right there, squarely, and were just about to sail into one of the ports. “Furl the sails! Tie the cables! Ready the oars!” Dean roared. “Drop anchor!”

Many sailors saluted while running from spot to spot on the ship to pull it into port.

Dean turned and watched the docks draw close to the ship and the anchor splash into the water. He grinned to himself, feeling his body twitch with excitement. “Don’t worry, Cas, I’m here.”

~  ~  ~

“Sam, can you and Charlie handle everything?” Dean asked, not being able to stand still. Sam scoffed.

“Get out of here you scoundrel,” Sam laughed pushing him down the dock stairs. Dean shot Sam a grateful look before he turned and sprinted away, following the same path he took to take Cas home the morning’s after they made love. The whole way there Dean was smiling and almost tripping because his legs weren’t going fast enough.

When he saw Cas’s house he almost screamed because he wanted so badly to be in Cas’s room right now, hugging and kissing him and telling him how much he had missed his blue eyes, plush lips, soft hands, and everything else that made up Cas.

He slowed himself down when he got to the wall he had to jump off of to grab onto the vines he had to climb up to Cas’s terrace. Dean made quick work of this and was pulling himself over the railing and pushing open the glass doors to walk into Cas’s room in no time.

“Cas…” Dean’s voice fell to a whisper and his dick twitched. “Fuck.”

The younger boy was in the middle of his bed, on his back, legs open and naked. Dean could see that Cas had fell asleep with the ivory plug in him.

Dean’s eyes wandered over to the nightstand next to the bed. The oil he’d given Cas was there with a slip of paper next to it. On further inspection, he saw it was a note for him:

 

_“Dean ~_

_I may be asleep by the time you get here, but it’s been too long._

_~ Cas”_

 

“Cas you perfect, _perfect_ angel. You were preparing for this,” Dean whispered, undoing his belt and crawling between Cas’s legs. He looked at the boy below him and felt himself becoming hard embarrassingly fast.

Dean grabbed the oil and pulled his member out of his pants to stroke himself, doing the same to Cas’s cock.

Cas didn’t wake up, but he started panting and clenching his hands around nothing. “Gods, Cas,” Dean gasped, keeping himself quiet so he could hear the little huffed out noises Cas was making. He did this until they were both hard and then he tapped the plug Cas had in him. A gasp was pushed out of the boy's lungs, making even more blood rush below his belt. He pulled the plug out and oiled up his fingers to test how stretched his lover was.

Dean couldn’t help the sharp intake of air he sucked in. Cas was so tight, but at the same time he was stretched enough to take Dean's cock. The older man lined himself up with Cas’s entrance and slowly pushed in, falling forward with his hands strategically placed by Cas’s ribs.

He thrust shallowly at first, loving the delicious little breathy whimpers leaving Cas’s lips. The noises Cas made during their nightly encounters was like a drug to Dean. He couldn’t get enough. It frustrated him that he couldn’t just fuck into him right here right now and drink in the screams Cas would let out.

Dean started to pull out farther and thrust in faster, making Cas start to wake up, letting punched out whines fall from his mouth as he fluttered his eyes open, taking a minute or two to focus on the man on top of him.

“Dean,” He whispered out a gasp. Cas’s eyes rolled up into his head and he let out a loud moan Dean had to cut short with his hand.

“Sh,” He whispered. Dean could feel Cas’s beautiful noises vibrating against his hands. He replaced his hand with his mouth in a swift motion, and kissed Cas as the boy’s hands and legs came to wrap around him.

“Dean,” Cas whimpered against said man’s lips, “I missed you - ah! - so much.”

Dean breathed out a laugh, “Me too, Cas, you have no idea.” They kissed again, pushing their tongues into each other’s mouths sloppily. Dean started thrusting into Cas harder and faster, stopping for a second to pull his belt out and tell Cas to bite down. “You can’t be loud here, unfortunately.” Cas’s head bobbed up and down as he muffled another cry of pleasure into Dean’s thick leather belt. “Fuck, we’re not doing this here again. I want to hear those beautiful moans you make,” Dean panted out. “Not stifle them.” He grabbed Cas’s hands and laced their fingers together.

The two kept their eyes locked onto each other as Dean drove his hips into Cas. Dean felt himself start to tear up from the pleasure he as experiencing by being with Cas again.

“Fuck, Cas,” Dean gaped, “I missed you so much. You don’t even know. It was so hard without you.” Cas whimpered, gripping tightly onto Dean’s hands as he let his legs fall open, giving Dean a better angle to plunge into him.

Cas could feel the rough fabric of Dean’s pants rubbing against his bare ass. It only took a few thrusts for Dean to find Cas’s prostate, making the boy below him arch his back and push his bare chest into Dean’s clothed one.

Only a couple thrusts later, Cas was coming - hard. Harder than he had the whole duration Dean was gone. He violently bucked against Dean, rubbing his cock against Dean’s abdomen through his orgasm, spasming as the material of Dean’s shirt scraped against his oversensitive cock. The noise Cas made through the belt when he bucked his hips pushed the man on top of him over the edge with a grunt.

Dean bottomed out as he came, gyrating his hips to rub against Cas’s length helping the boy through his orgasm and making him convulse against Dean.

When Cas’s hips started to jerk erratically, and his arms and legs started to quiver, Dean slowed down before stopping altogether. He pushed his face into Cas’s neck and peppered the skin there with wet open mouthed kisses. The two stayed like that for a few minutes before Dean shook his hand free of Cas’s and pulled his belt out of the boy’s mouth, making him sigh.

“Bloody fuck,” Dean said breathlessly. He kissed Cas deeply, moving his lips in just the right way to make Cas gasp for breath.

“Dean,” Cas breathed his name out like it was a prayer, looking into Dean’s eyes the whole time. “Dean… Dean… Dean…”

“I missed you, baby, so much. I can’t tell you how much.”

Cas nodded, “I felt to empty without you.” A few tears slid out of his eyes. Dean cupped Cas’s face to wipe them away. “It was so bleak.” Cas turned his head in Dean’s palm and closed his eyes. Dean pressed his forehead to Cas’s temple.

“I’m so sorry.” He closed his eyes.

“I was so worried I wouldn’t see you again.”

Dean let out a shaky break, “Me too, Cas,” he whispered. “I never stopped thinking about you.”

Cas’s chest heaved, “I don’t want you to leave again.”

Dean lifted his head to look at his Cas. “I’m not leaving. I’ll never leave you.”

Cas shook his head and let go of Dean’s hands to clung onto the collar of the taller man’s overcoat. “But you will. Sooner than later you’re going to leave again.”

It was Dean’s turn to shake his head. “Nay, Cas.” Dean reached into his pocket and pulled out a small teardrop shaped stone with silk string tied around it.

“A necklace?” Cas asked.

Dean nodded. “I’ll always be with you. I found this on the shores of an island I named after you. It’s the only one known to the world. I made sure, too - took it to a specialist. He said I needed to name it... Do you know what I named it?”

Cas shook his head, looking at the beautiful vibrant green and blue swirled gem. “What’d you name it?”

“This gem - the only one known to man and came from the island of _Castiel_ \- is named Angel’s Eye,” Dean whispered, keeping his eyes on the boy below him the whole time.

“Dean,” Cas gasped. He pulled Dean down for a kiss while the man on top of his stretched his arm out to put the necklace on Cas’s nightstand before bringing it back to rub Cas’s side.

“Whenever I’m out at sea,” Dean said as Cas kissed down Dean’s jaw, “Wear this, and I’ll always be with you. It’s also an early birthday present of sorts. So, happy early birthday.”

“Dean,” Cas moaned, rocking his hips against Dean’s and feeling the man twitch inside him. “I want you to make love to me again.”

Dean’s breath caught in his chest as the feeling of Cas moving his hips. “I’ll make love to you all night, if you want me too.”

Cas nodded at Dean, biting his lip. “Touch me, please.”

“Whatever you what, angel,” Dean whispered, reaching his hand down between them to take Cas’s length into his hand. He gave Cas a gentle squeeze, relishing in the feeling of being able to touch him again. He slowly stroked Cas while rocking his hips.

“Take—” Cas screwed his eyes shut and gripped onto Dean harshly as a spasm ran through him. “Take your clothes off.”

Dean chuckled when he realized Cas was completely naked and he was completely clothed. “You want to help me?” Cas nodded his head, moving his hands to practically rip Dean’s shirt open before putting them against his chest and running them over as much as the skin as he could.

“You feel so _good_ ,” Cas whispered, closing his eyes and feeling the skin beneath his hands. He heard Dean laugh and he opened his eyes halfway to see Dean staring down at him adoringly. “What?”

“You’re getting hard just from touching my chest,” Dean said, smiling warmly at him.

“You’re also touching me, Dean,” Cas pouted and wiggled his hips, making Dean groan quietly. “Now look who’s getting hard.”  

Dean laughed again, “Gods, I missed you.” He sat up and shed his top layers off before slowly pulling out of Cas to take his bottom’s off. Dean was about to push back into Cas, but the smaller boy stopped him by nudging his shoulder to flip them over.

“Whatever you want,” Dean breathed out, grabbing onto Cas’s hips and rolling them so he was lying beneath Cas. His fingers never leaving the blue-eyed boy’s hips.

Cas slid down to straddle Dean’s thighs, wrapping his hands around Dean’s impressive length. “You’re so big.”

“I’ve been told.” Dean smirked. He put his hands behind his head and closed his eyes, letting Cas take control.

Cas caressed Dean, loving how amazing it felt to have him in his hands again. For a moment, he wished he could be with Dean everyday so he could reach into his pirate’s pants whenever he wanted to feel the manhood he craved. But right now wasn’t the time to be thinking about the future. He only wanted to worry about the present.

After a while, Cas moved further down Dean’s legs so he could take the head of Dean’s cock into his mouth. When he did, he heard Dean hiss and his hand came down to run through Cas’s hair.

“Fuck, Cas,” Dean cursed, “I almost forgot how amazing you are with your mouth.” Dean’s admission made Cas smile and pick up his pace. He decided he was going to make Dean come and he was going to swallow all of his release down, savoring the taste. After all, it had been five months since he was able to enjoy Dean’s cum.

Dean’s hips twitched. “If you don’t stop I’m going to come,” Dean said, his words light and airy. Cas picked up his pace and hollowed his cheeks almost violently. But Dean didn’t come, instead he pushed himself up onto his elbows to watch Cas. “Fuck, are you trying to make me come?”

“Yes,” Cas said breathlessly around the head of the taller man’s cock. He looked up at Dean through his lashes.

Dean let out a breathy laugh, “You look so innocent doing that with your eyes.” A moment later, his mouth dropped open, his eyes closed, and then threw his head back as he came. Cas moaned loudly, swallowing down every last drop of Dean’s come.

When Dean’s hips jerked, Cas stopped and placed little kisses along the man’s shaft, giving one last good suck around Dean before pulling off. Cas sat up and let go of Dean’s softening cock. He rubbed his tongue along the top of his mouth, doing his best to remember the exact way Dean tasted when he came.

“You look so fucking hot like that,” Dean said quietly, still on his elbows when Cas opened his eyes.

“You taste so good,” Cas explained, “I wanted to make sure I can remember it when you’re gone.”

Dean’s eyes clouded as he pushed himself to sit all the way up. He grabbed Cas’s hands and pulled him into a kiss, sucking Cas’s tongue into his mouth and swallowing the moan it elicited from Cas.

“May I try something new to you?” Dean asked, breaking the kiss. Cas nodded, making Dean smile. He put his hand over Cas’s mouth and flipped them blindingly quick, making Cas yelp into Dean’s hand. “Lay down on your stomach.”

Cas blushed as he got into the position. Dean nudged his legs open and settled himself between them before grabbing Cas’s hips and pulling him onto his knees, completely exposing Cas to the broad man. Cas gasped and buried his face into his pillows to hide his blush.

“You’ll need to keep your mouth covered,” Dean said in a breathless voice. Cas felt his thighs trembled with anticipation. Cas nodded, biting down on the edge of one of his pillows.

Cas closed his eyes and waited to feel Dean’s fingers at his entrance, but the next thing he knew he was pitching forward while yelping into his pillow. Dean had used his tongue to push into his hole. He could feel Dean’s stubble scratching at the most sensitive skin he had.

Dean pulled away, tracing his finger around Cas’s rim. “Feel good?” He asked.

Cas nodded. “Feels so good.” He tried to say, but didn’t trust himself to let go of his pillow. Dean snorted softly before going back and eating Cas out.

He didn’t stop until his tongue was cramping and he felt his cock starting to ache against his stomach. Dean pulled away, almost coming right then from the whimper Cas made. They boy was too far gone in his pleasure; he couldn’t form words. “It’s okay, I got you.” Dean grabbed the oil again and poured some onto his length before adding some more on his fingers and using that to lube Cas up. And when he was satisfied with it, he slowly pushed into Cas, rubbing up and down the sides of the boy’s torso.

When he was all the way in, he draped himself over Cas and found the boy’s hands, intertwining their fingers again. “Ready?” He asked, placing small kissed between Cas’s shoulder blades.

Cas pressed back against him, nodding his head curtly. Dean started out slowly; he knew Cas could come just from his cock, and he wanted to draw out his angel’s pleasure for as long as possible. He only sped up his movements, thrusting harder and faster, when Cas started to twitch around him. He got to the point where he pushed Cas up into the bed with every thrust.

Dean leaned down to whisper in Cas’s ear. “Feels so good to be back with you, baby. I love being able to make you feel so good you don’t even need to be touched to come. Do you want to come?” Cas’s whimper could be heard perfectly in Dean’s ears despite his mouth being clamped down on a pillow. “C’mon, angel, come for me.” Dean had to keep himself pushed against Cas’s back to keep him from rising up and screaming out as his orgasm crashed through him.

Dean slowed down, stopping completely when Cas lifted his head. “Don’t,” Cas whined, his voice was hoarse and wrecked. Dean thought he was too strung out for Dean to finish inside of him.

“I know, baby, I know,” Dean started to pull out to finish himself off, but Cas grabbed his arm urgently.

“Don’t,” He whined again.

“Cas, you just came,” Dean protested, “I don’t want to overwhelm you too much.”

Cas looked back at him with wet eyes, “Keep. Going.”

Dean didn’t need to be told twice. Cas bit down on his pillow again and Dean pounded into him. He could hear Cas’s cock slapping against the his stomach. The taller man felt himself coming undone, he had to grab onto Cas’s hips to ground himself.

A few more thrusts and that was it for Dean, he came with a violent thrust into Cas’s unbelievably tight heat and a skin breaking bite to his lip to keep himself from moaning. He fell against Cas’s back, spent and sure that Cas was completely spent as well.

“Cas,” Dean kissed up along the boy’s spine, pulling out slowly. “Cas you’re so perfect.” When he reached the nape of Cas’s neck he pushed himself onto his knees and helped Cas to lie down on the side of the bed that wasn’t covered in cum and sweat. “You’re so beautiful.” He kissed Cas gingerly, running his hands through his hair before getting off the bed and grabbing his already cum soiled shirt to clean his angel up.

“Dean…” Cas mumbled, reaching out for him. “I think… I think I… I’m falling...” He didn’t finish. Dean smiled and watched as Cas began to snore; louder than Dean had ever heard him before.

Dean finished cleaning Cas and himself up before he picked the smaller boy up, careful not to wake the sleeping angel, and got under the covers with him.

Both of them slept better than they had in months.

~  ~  ~

_February 14, 1693_

 

Cas woke with a start, only calming down when he still felt the warmth of his pirate behind him. He was glad Dean hadn’t left during the night. If he had… Cas wouldn’t’ve believed last night was real.

“Good morning,” Dean said, his voice groggy and very deep. Cas turned around in the pirates arms and kissed him.

“I’m so happy to see you,” Cas whispered.

“Me too,” Dean pecked the top of Cas’s head before he rolled onto his back and stretched. After than, he got up and started to pick his clothes up.

Cas watched him, admiring how handsome his form was. He frowned when he saw the disgustingly deep scar that ran from right under the nape of Dean’s neck to just above his tailbone. “Dean,” Cas questioned. He saw said man tense up.

“Shit,” He breathed out quietly.

“What happened?” Cas asked. He got up and warily traced the scar along Dean’s back. He felt Dean tense up again and begin to move away. Cas looked at the back of Dean’s head before he saw the man lower it and his shoulders set in an shameful way. Cas got the feeling that this scar was something Dean was disgusted by.

Cas moved his hands away from the scar and onto Dean’s shoulder blades. “It’s so…” Cas struggled for form words. “It’s so-”

“ _Ugly_.” Dean clenched his fists. Flashes of the months upon months Alistair took to continuously open his skin up to his spine ran through his mind.

The next thing he knew, Cas was hugging him, his face pressed into his back and his lips kissing his scar.

Dean heard Cas whisper against his skin. “I’m sorry.” Cas could tell this scar was something Dean was ashamed of. He didn’t understand how he knew, but he did. Dean was ashamed of this mark on his skin… And Cas didn’t need to hear Dean say how he got it to know that it was something Dean wholly loathed about himself.

“I’m — It — I…” Dean couldn’t speak. He was sure Cas wouldn't want to stay with him now. Not after he'd seen what a monster Dean was.

“Dean-” Cas started.

“I wouldn’t blame you.” Dean found himself saying “If you… If you don’t want to see me again.” He knew it was crazy. What had happened to him wasn’t his fault; he knew that. But it didn’t lessen the sporadic thoughts he had of not being good enough for anyone. “I know it’s hideous.” He has to take some deep breaths before speaking again. “I know _I’m…_ ” Dean couldn’t finish. But his intended words hung in the air.

Cas gasped, “No.” Dean felt more hesitantly placed kisses on his back. “You’re _not_. You’re not.”

“Cas,” Dean shook his head in shame. “You don’t know the story behind it.”

“I don’t have to, Dean,” Cas said firmly as he came to stand in front of Dean. But the taller man couldn’t meet his eyes.

“You don’t understand.” Dean closed his eyes and kept his arms at his side. “That… _thing_ on my back… I got it—” Cas silenced him with a kiss. Dean felt Cas nudge him back to sit on the edge of his bed before climbing into Dean’s lap, hugging him tightly and not letting go.

“I don’t care how you got it,” Cas whispered, kissing anywhere on Dean’s face while he traced the edges of the scar. “It doesn’t matter how you got it.”

“I’m—” Dean cut himself off. His arms slowly came around Cas and his shoulders started shaking.

“Dean, it’s okay,” Cas hugged onto Dean, and let the man cry into the crook of his neck. Dean’s hands were splayed open on his back, one between his shoulder blades, and one on the small of his back.

“Cas...”

“You’re not ugly,” Cas whispered, pressing himself further into Dean, “You are beautiful.” Dean was shaking Cas with the force of his sobs, but Cas didn’t mind. He held Dean close, one hand holding onto the hairs at the back of Dean’s head and the other gently massaging along his spine. "You're absolutely stunning." 

Cas continued to whisper to Dean, feeling the man's shaking come to a stop before small kisses were placed on his neck. Dean slowly kissed his way over Cas’s neck for a few minutes before he started to suck. Cas could feel Dean starting to get hard again.

“Dean,” Cas sighed blissfully, “You’re libio is unquenchable.”

“Are you able to go again?” Dean mumbled against the skin of Cas’s neck. His voice was still laced with sadness and shame.

Cas’s head tilted back to expose more skin for Dean. “For you, always.”

The next thing Cas knew, he was on his back on the edge of his bed with Dean kissing down his chest, stopping to play with his nipples before continuing down. He put his hand on Cas’s stomach and lifted his head.

“Who’s in the house?”

“My father isn’t,” Cas said Dean smiled and pushed the boy’s legs onto his shoulders. “It’s Friday?”

“Yes,” Dean responded.

Cas smiled. “My mom’s taken the kitchen staff with her to the market to shop. And the cleaning staff gets Friday off.”

“Good,” Dean growled. In the blink of an eye he had his mouth on Cas’s length and was bobbing his head at a blinding pace. Cas could feel himself begin to lose his mind as well as control of his vocals. His hands threaded themselves into Dean’s hair and tugged roughly, making Dean moan around him and Cas to let out a loud yelp. But all too soon, Dean pulled off and crawled back up to kiss him deeply.

“Please,” Cas begged Dean; he didn’t have to say what he was asking for, Dean understood. He skillfully leaned over Cas and grabbed the bottle of oil, making quick work of dipping his fingers in and pushing two at once into Cas. “Dean!” Cas whined loudly, pulling again at Dean’s hair. He pushed his hips down to meet the thrust of Dean’s hand for a few minutes before almost violently tugging Dean’s head to the side. “More!”

“Whatever my angel wants,” Dean panted, adding another finger and rubbing against Cas’s prostate. Dean watched Cas’s face contort and his chest heave. “Gods you’re so fucking beautiful.”

Cas arched his back, “Stop, I’m gonna come!”

“Then come,” Dean said lowly, almost as a command.

“No,” Cas whimpered, “I wanna come on your cock.”

“Fuck, Cas,” Dean growled before removing his fingers and coating his manhood generously with oil. Cas whined when he didn’t feel Dean push into him right away. He yelped when he felt himself being picked up off the bed and pushed into the wall next to the doors that led to his terrace.

“Lock your ankles behind my back.” Dean growled into the boy’s ear. Cas quickly obeyed looking into Dean’s eyes, seeing a wildness in there that made his cock leak a generous about of precome.

Cas made a pathetic little “huh!” sound when Dean finally thrust into him, as if all the air from his lungs was being pushed out of him. He had a hard time catching his breath after that. Dean used one hand to reach between them and tease Cas’s length with feather light touches while the other supported some of Cas’s weight, gripping onto the back of the smaller boy’s thigh; hard enough to leave a bruise.

“Ah!” Cas mewled, his mouth falling open and his breaths to be punched out of him in delicious little airy whines that had Dean craning his head down to suck a dark purple bruise into Cas’s collarbone. Cas gripped onto Dean, trying to move his hips to meet Dean's thrusts. But gave up when Dean's hips pounded faster and harder into him, hitting his prostate with every thrust. Cas yelled out Dean's name as his back scraped deliciously against the wall behind him. “Oh, Dean!” he gasped for breath, so close to coming his arms were like jello and he had to concentrate hard on keeping his ankles together. Dean must’ve been able to read Cas’s mind because right then and there he slowed his hips and let go of Cas’s cock and moved it to grip onto his other thigh. “No!”

“Sh,” Dean shushed, kissing Cas, leaving him gasping for more.

“Dean,” Cas’s voice was broken. His head lolled back against the wall and his eyes squeezed shut. He wanted to come so bad, but Dean wasn’t letting him. The head of the older man’s cock brushed teasingly against Cas’s prostate with every harsh thrust.

Cas began to forget his own name with the unsatisfactory rate Dean was going at. He just needed Dean to pound into him relentlessly until he passed out.

“Please,” Cas pleaded, saying the word over and over again. Dean smirked at the begging mess he’d reduced Cas to. “Please… Please, _Captain!_ ”  

Dean’s hips stuttered. “Say that again.”

“Captain!” Cas yelled, gripping Dean’s hair. “Please, Captain!” With a sneer and feral growl Dean pounded into Cas so hard he left the boy seeing stars. Cas’s legs quivered and he wasn’t able to keep them locked at the ankle behind Dean’s back anymore.

“Yes, please, right there Captain!” Cas was screaming his throat sore. “Captain!” His head fell forward to look Dean in the eyes. “ _Captain_ you’re making me come!” With that his eyes rolled back into his head and his mouth hung open while his whole body contracted with the force of his orgasm, pulling Dean over the edge with him.

Cas’s body slumped onto Dean, seizing every few seconds in violent curls around the pirate's body. Dean cradled the boy to his body and delicately carried him over to the bed and laid him down, not pulling out of him just yet; every time Cas spasmed, he clamped down on Dean’s cock, milking it for everything it was worth. He was still riding the waves of his own frenzied release within the boy’s heat.

Cas moaned his eyes still screwed tightly shut, his breath catching in his throat as a particularly violent convulsion hit him and had him clinging to Dean with his face pressed into the man’s neck. He let out a string of nonsensical sounds, muttering about nothing and everything to Dean.

When Cas’s eyes finally drifted open and focused on Dean, it was minutes after he’d stopped convulsing under Dean. He had a dopey grin on his face. Dean noticed that there was some of Cas’s drying cum on the boy’s cheek and in his hair.

“How you doing?” Dean asked, wiping the cum off of his face and hair and onto the bed spread.

Cas wasn’t able to speak just yet. “Mmh,” He hummed in response while lazily letting his hands drop from Dean’s hair and onto the bed by his head.

“You won’t be walking right for a week,” Dean muttered, finally pulling out of Cas who let out a long high pitched moan that sounded suspiciously like Dean’s name. Cas slurred out some more words that didn’t make sense and then pouted, taking deep breaths and frowning.

“What?” Dean asked, his brows furrowing, thinking he may have hurt Cas. “Are you okay?”

“Hmph,” Cas huffed out, his chest rising. He reached up, almost poking Dean in the eye trying to grab whatever of Dean’s head he could — Dean’s his ear, he’d later come to learn — to bring the man’s lips down to his own. Dean smiled into the kiss and continued to move his lips against Cas’s until his chest began to burn from lack of oxygen. Cas was breathing hard against Dean’s mouth and whining for more contact.

“You’re so fucking beautiful,” Dean murmured into Cas’s ear, nuzzling his hair with his nose.

“You’re…” Cas was still trying to gather his strength. “...beautiful.” Dean chuckled as he pulled back and looked at Cas’s blissed out face, memorizing every detail. Cas just blinked slowly up at him, smiling with his whole face.

“Cas…” Dean breathed out his name, putting his hand against Cas’s face and using his thumb to trace over his plump pink bottom lip. “You’re the best thing that’s ever happened to me.” The boy’s face glowed, up and his eyes crinkled at the corners as he pulled Dean into his body and embraced him. They stayed like that for a long while before hearing Cas’s door open. Both of them snapped their heads to see who it was: a rather short man with dirty blonde hair and an appalled expression on his face stood there.

“Castiel!?” He yelled, not moving.

“Gabe!?” Cas yelled, he scrambled to push Dean off of him and grab anything to cover himself.

“Castiel! What the hell?!” The short man gaped at Dean and Cas.

“Gabe! It’s Dean!” Cas yelled. Dean, who had gotten up and was standing — naked — looking between the two Novaks.

“Dean?!” Gabe shouted, looking over to Dean. “Dean _Winchester_?!”

“Yes!” Cas almost fell off the bed as he scrambled to his dresser, sparing a look at Dean. “Dean! Clothes!”

“Castiel!” The man, Gabe, stared at Dean’s manhood with wide eyes. “He’s hung like a goddamn fucking horse!” Gabe’s eyes shot over to Cas as he pulled a shirt over his head and looked him up and down. “You're so small! How do you—!”

“Gabe, please!” Dean knew Cas was blushing profusely. Gabe ran a hand through his hair and pivoted around.

“Fucking hell! Get dressed you two.” He walked out of Cas’s room and slammed the door. Neither Cas or Dean spoke for a few seconds.

“I’m so sorry,” Cas whispered, covering his face with his hands. Dean shook his head and bent over to pick up his pants.

“Don’t worry about it.”

“God that was so embarrassing.”

Dean smirked while pulling his trousers up and tying them. “Well, I mean, at least he complimented me.”

Cas looked at him with a pained expression. “That was my _uncle_.”

“Oh..." Dean said, nodding. "So you told him about us?”

“I'm sorry. I had to. He’s the only one I told and he won't tell anyone else, trust me."

"I trust you," Dean said, smiling comfortingly.

"Thank you... It's just... He helped me through my rough patch when you were gone. If not for him... I would’ve most likely never have left my room.” Dean’s expression turned into a frown before he walked over to the nightstand next to Cas’s bed and held up the necklace he’d gotten for Cas.

“May I?” he asked. 

“Of course.” Cas looked at him and nodded his head. Dean walked over to Cas and hugged him tightly before kissing him and putting the necklace on. Cas walked over to his mirror and looked at it on himself. Dean followed him and wrapped his arms around Cas’s waist.

“How do you like it?” Dean whispered, inhaling the scent of Cas.

“I love it,” Cas responded and leaned into Dean’s embrace. The two of them stayed like that for a good while, swaying slightly and enjoying each other’s company.

“You better not be fucking around in there!” The two males heard Gabe call from outside Cas’s room.

Cas jumped slightly and nodded. “We should, uh, you should get dressed.” He looked at Dean’s shirtless torso longingly through the mirror.

“Probably,” Dean whispered, giving Cas a quick peck on his temple before letting go to pick his coat up off the floor and pull it on. Cas watched him with lust-blown eyes.

“What about your shirt?” Cas asked, looking a little flustered.

“I used it to clean us up last night.”

“Oh,” Cas breathed out. He shook his head and nodded. “You can come in, Gabe!”

“Castiel,” Gabriel immediately started talking, “What the fuck is going on-?” He stopped short, looking at Cas’s bed. Dean followed his gaze and saw the mess the two had made on the comforter last night. No one was speaking. Gabe had clammed up, unable to look anywhere but Cas’s ruined bedspread. Cas was covering his face with his hands again. Dean took this opportunity to break the ice.

“Hello,” Dean walked over to Gabe and stuck his hand out. “I’m Dean Winchester.”

Gabe looked at him. “No shit.”

“Gabe!” Cas pleaded. Gabe rolled his eyes and shook Dean’s hand. Not letting go for a long while; just darting his eyes between Dean’s green ones.

“Dean Winchester,” Gabe started, speaking slowly and clearly, “Let me get one thing straight right here, right now. If you hurt Castiel, I will kill you.”

Dean smiled at him, “To be square, Gabe, I don’t plan on hurting Cas.” He let go of the man’s hand.

Gabe scoffed. “What do you plan on doing with him then? If you’re just using him for sex then you need to leave.”

“God, Gabe!” Cas gasped. 

Dean furrowed his brows, “What?”

“If you’re just acting like you like him just so you can get to Michael, then stop. Cas deserves more than that.” Gabe ground out, looking like he was going to throw a punch.

“Gabe,” Dean backed up, “Nay. I would never.” Gabe looked him up and down, judging ever part of him.

“Then what the fuck are you really doing with him? He’s not some piece of ass you can just fuck and ditch for months while you’re out fucking whoever else you want to.”

“Gabe!” Cas shouted, sounding angry himself.

“What’s your problem?” Dean asked, squinting his eyes at the shorter man. “I’m not using Cas. I care about him.”

Another scoff left Gabe’s mouth, “Yeah, right. You really show it by the way you left him for five months! Do you even have any idea how hard it was for him?” Gabe stepped right up to Dean. For a short guy, he sure could be scary.

“I didn’t want to leave,” Dean shot back. “I had to!”

“Gabe, please!” Cas tried to push his uncle away from his lover.

“Why don’t you just leave, _pirate_?” Gabe spat the word out like it was poison.

Dean roared, “Cas is the best thing that’s happened to me in my whole life. It tore me apart to leave him. But I have responsibilities!”

“Right, responsibilities to kill and murder others for gold,” Gabe laughed dryly.

Dean sneered. “For starters, responsibilities to my crew! I can’t just leave them.”

“You’re wasting Cas’s time.”

Dean lunged at Gabe. “Shut up!”

Cas stepped in front of Dean, putting a hand on his face and effectively stopping him in his tracks. “Dean.”

“You don’t know me! I respect and cherish Cas! You don’t understand how I feel for him! I’m crazy about him!”

“Dean, please,” Cas whispered, forcing Dean to look into his eyes. “He’s not being serious.” The Pirate King looked deeply into Cas’s eyes and found himself calming down. “He’s testing you.”

“He’s testing me,” Dean repeated, focusing on the soft hand on his face and the blue eyes staring into his.

“He doesn’t mean what he’s saying,” Cas moved his hand to the back of Dean’s neck.

Dean found himself nodding. “Okay.”

“Are you calmed down, now?” Cas pressed his other hand over Dean’s heart. The taller man closed his eyes and breathed deeply, nodding.

“Yes, I’m sorry,” Dean whispered, putting his hands on Cas’s waist.

“Good,” Cas smiled before turning to Gabe. “You need to apologize, too.”

Gabe shrugged and walked over to Dean, clapping him on the arm. “I’m sorry. I just wanted to make sure Cas was in good hands.”

Dean forced a smile onto his face. “No problem. All is forgiven.” His words came out harsh and insincere.

“Dean, do you need to go?” Cas asked, looking behind him at his wall clock. Dean followed his gaze before his shoulders dropped and he nodded his head.

“Yeah.” Dean looked back at Cas, taking his hands in his own. “I’ll see you tonight?”

Cas nodded, “I’ll come to you.”

Dean smiled, leaning down to tenderly kiss Cas on the lips. “I can’t wait.”

“Yeah, me too. But Castiel we gotta go. Your father actually has something planned for you in an hour,” Gabe interjected. Cas rolled his eyes and kissed Dean once more before letting him go.


	5. Chapter Five

**Summary for the Chapter:**

> Cas's birthday is approaching and Dean seems to have something planned. Right as things are about to get steamy between the two, a woman comes along and is hysterically asking to see Dean. Long story made short (as to not give away key details) Dean's got two more people in his crew by the end of the day. 
> 
> But that good news comes with some bad news: Cas's father has hurt Cas again and it's not just a few kicks to the ribs this time.

**Notes for the Chapter:**

> TW: abuse, (mild) objectification of women.

Chapter Five

_February 16, 1693_

 

Dean’s first week back from sea went by in a blur. The two saw each other whenever they could and spent the majority of the time talking and laughing together, as well as getting to know Dean’s crew better. At one point Cas even risked sneaking out of one of his father’s town meetings to see Dean and his first mates during the day.

“What do you want to do for your birthday?” Dean questioned, turning his head to look at Cas, who was using his arm as a pillow. “It’s next week.”

“I don’t care. I just want to spend it with you.”

“Can you sneak away for the day?”

“My dad’s leaving for a business trip the night before and won’t be back for a few days. He’s been talking about it non-stop. He’s going to meet with the Crowley family from the Royal Kingdom about a new proposal to make Heaven an extension in their kingdom. He’s trying to offer them a priceless heirloom we’ve kept in the family for generations to make up for me missing the previous meeting and _'wasting the Kings time,'_ as my father put it. The only reason I'm  not going is because Michael thinks I'm going to thwart his attempts to repair the irreparable." Cas sighed. "Oh well. He's just... He's... Stressed."

Dean rolled over on top of Cas, “Aye, I mean, of course; he's only trying to unite Heaven and the Kingdom so he can use Crowley's militia to get me hanged." He smiled at Cas jokingly. "I understand how stressful that must be."

"Agreed," Cas giggled. "But that also means he won't be around for my birthday or the day's after it."

"So you could just come here the night before, like usual, and then spend the weekend with me?”

Cas smiled and wrapped his legs around Dean’s hips. “I _could_ , yes.”

“ _Will_ you?”

“What do you think, _Captain_?” Cas teased, prompting Dean to raise an eyebrow deviously before diving his head in too mouth at Cas’s collarbones. The younger boy loved when Dean would suck bruises into his skin; he liked being able to have physical evidence of Dean having touched him. He liked being able to feel and see the proof of the older man.

“Do you want me to mark you?” Dean asked.

“Yes,” Cas said. He spread his legs farther apart to let Dean settle between them more comfortably. Dean immediately started sucking red blotches into his skin.

Cas’s father had left early for a day trip to a neighboring town to prep for his trip to the Royal Kingdom next week; meaning, Cas was excused from his schooling and court observations around midday. Furthermore, he got to meet with Dean and have a hike in the woods together.

After that, they snuck onto Dean’s ship and Cas helped with some of the repairs. That had been around five in the evening. Now, it was eight; and they’d spent the last hour and a half together on Dean’s bed, half-naked and only shedding more clothes when the temperature got to be too much under the covers.

Dean was seconds away from attacking Cas’s chest with more hickeys and pushing his hand into Cas’s linens when someone pounded at his door. He groaned in frustration as he got up to answer it. Cas sat up on Dean’s bed and pulled the first shirt he found over his head. Judging by how it wouldn’t stay on his narrow shoulders he guessed he had put on Dean’s shirt.

Dean flung the door open and snapped, "What?!" He stood there with his shirt off and only his leather pants on. Cas couldn’t see who it was, but he knew the voice: Benny.

“There’s a lady here to see you, she’s hysterical. Crying about how they took her baby away.”

“Did you get a name?” Dean asked, sounded rather annoyed. Cas got up and walked over to stand behind his pirate.

“Lisa Braeden.”

Dean breathed out, “Well shit.” He turned to Cas, “Stay here, okay?”

“What? No, I’m coming with you.”

“It’s okay, I just have some business I need to attend to.” Dean gave a reassuring smile.

“I want to come with you,” Cas insisted. “Please?”

Dean sighed, “Okay, but stay behind me. I don’t know what’s happened.” Cas nodded, taking Dean’s hand in his own and following him to the main deck. The closer they got, the easier it was to hear the devastated sobs of a woman.

Upon walking onto the deck, Cas was able to see that it was one of the citizens that worked in the whore houses. He’d seen her multiple times in front, waving at men as they passed and batting her eyes flirtatiously. Cas felt a pang of jealousy course through him. _Had she and Dean been intimate together?_  But he quickly pushed that thought away; it was ridiculous.

“Lisa?” Dean questioned the lady once they were able to see her. She was sobbing to some of the swabs about how she needed to see Dean.

“Mister Winchester!” She ran at him, throwing her weight against his body in a sobbing mess. Dean had to let go of Cas’s hand to catch her; he fell to his knees in the process with the woman in his arms. “They took him!”

“Took who? Lisa, calm down, I can’t understand you.”

“They took my baby! They said I wasn’t providing for him and they took him!” She howled with pain.

“Ben?” Dean responded, his voice as sharp as nails. “Who took him?”

“The guards! They found us huddled together in the crossroads between alleys and said I was an unfit mother. I’ve lost my job at the Brothel - Constable Uriel was one of my regulars, he knew I’d been kicked out and-and he t-took my baby!”

No one spoke while Dean consoled the woman into quieting her sobs. “Lisa.”

“Please, you have to help me — I’ll do anything! You don’t know what the orphanages are like.”

“Lisa, calm down.” Dean rubbed her back, “Why don’t you get a full night of rest, and we’ll go get Ben back tomorrow. I promise.”

She nodded, putting her hands on the sides of Dean’s face. “Thank you.”

“I’ll get you whatever you need, too, Lisa.”

“Thank you, Mister Winchester,” She threw her arms around Dean’s neck, “Thank you so much!”

“Don’t worry about it,” Dean soothed. “And you can call me Dean.” He helped her up and asked for Benny and Charlie to let her into his own cabin to sleep. After she was out of sight, Dean turned to Cas.

“That was—”

“I’m sorry,” Dean interrupted. “I let her have my bed. I saved her son the last time I was here and offered her my help if she ever needed it. She looked like she could use it.”

Cas smiled warmly at him, walking over and sliding his arms around Dean’s waist. “It’s okay.”

“I know things had been gettin’ hot in there,” Dean talked quietly so no one would overhear. “I mean, I was just about to get in your pants.” Cas blushed and looked around, making sure no one was paying attention to them. Dean snickered and winked at Cas when he looked back at the taller man.

“Well,” Cas bit his lip, “There’s no reason we can’t go somewhere else.”

Dean raised his eyebrows, “I love the way you think.” Cas smiled and snaked his arm up to pull Dean down to kiss him. “Where do you want to go?” Dean asked between kisses.

Cas smirked, “What about going to the forest behind my house? Where you usually drop me off at in the mornings.”

Dean took Cas’s hand in his own, “Abso-fucking-lutely.”

“Let’s go,” Cas said, squeezing Dean’s hand in his own. Dean nodded, taking Cas to grab a quilt for them to lay on before heading out; laughing with each other while they ran off on the path they usually only travelled on in the early hours of the morning.

~  ~  ~

“Dean?” Cas moaned while arching his back into Dean’s bare chest.

“Yes,” Dean whispered, dragging his thumb across one of the boy’s nipples, “Cas? Do you need something?”

Cas gasped, tugging on Dean’s hair and encircling his legs around Dean. “I want — ah—!” Dean cut him off with a harsh pinch on his nipple. “Ah, Dean!”

“You want?” Dean encouraged Cas, moving his other hand under the baggy shirt Cas was wearing to tease at his other nipple. Cas wasn’t able to respond, he yelped and pushed his chest farther into Dean’s hands. “I didn’t know you had such sensitive nipples; I mean, I knew they were sensitive, but I didn’t know they were _this_ sensitive.”

“Dean!” The blue-eyed boy almost yelled. Dean pushed the shirt up to expose Cas’s chest and took on of the sensitive nubs between his teeth, gently biting down. “ _Dean_!” Cas felt his hips lift into Dean’s.

“Cas,” Dean breathed out, his mouth still teasing Cas’s nipple.

“Dean, I—” Cas tried again to formulate a coherent sentence. But, again, was stopped short by Dean’s mouth on his chest. His head fell back as he moaned and arched his back further upwards. In a swift motion, Dean closed his lips around the bud between his teeth and sucked harshly. Cas let out a howl, “Stop!”

The pirate pulled back, worry written on his face. “I’m sorry. Did I hurt you?”

Cas shook his head before he made Dean sit up. “No,” he said breathlessly, “I just… I can’t talk when you do that.”

“Are you sure? I wasn’t too rough?”

“No,” Cas said. “I really liked it. I just… I want to try riding you, again,” he rushed out, resisting the urge to turn his head away from Dean to hide his blush.

“What?” Dean asked dumbly.

“Sit up,” Cas instructed, pushing the older man into a sitting position before he straddled his lap. “I want to ride you.”

Dean broke out in a grin, “Okay.” He put his hands on Cas’s hips and rubbed circles with his thumbs into the skin there.

Cas smiled back, “Yeah?”

Dean nodded, “Yes.” He pecked Cas and reached into the pocket of his discarded pants to grab the oil. “You want me to prep you first?”

“Dean,” Cas said, “You realize that I haven’t needed to be prepped for the past three days, right?”

Dean shrugged, “Maybe I just like fingering you.”

“Shut up,” Cas giggled as he pushed Dean down onto his back. “I want you in me.”

“Oh, boy; you’re so spoiled,” Dean joked.

“Who’s fault is that?” Cas teased, moving down to straddle Dean’s thighs. He grabbed the oil from Dean’s outstretched hand. Dean put his hands behind his head for support as Cas tugged his drawers off.

“I take no responsibility for that,” he said closing his eyes and sighing when Cas made quick work of lathering his cock with the oil, making sure to drip a little extra on.

“Ready?” Cas asked, scooting up again, sitting up on his knees and reaching behind him to guide the head of Dean’s cock to his entrance.

Dean cracked an eye at him and raised an eyebrow, “Do you really have to ask?” Cas smiled shyly and nodded, lowering himself down very slowly. His mouth fell open and a quiet gasp left his mouth.

_“Oh!”_

“Fuck, Cas,” Dean’s hands came to rest on the boy’s hips. “I have no idea how you manage to stay so godsdamn tight.”

“Oh, my god,” Cas gasped. He put his hands on Dean’s chest and leaned forward while his eyes fluttered closed. “Oh, my god!” Cas was on the verge of being overwhelmed. He didn’t know why, but this position just made everything more intense and he was still so new to all these sensation. Part of him thought he'd never get used to the feeling of Dean filling him up so fully.

“You look so fucking beautiful like this, angel,” Dean breathed out, rubbing Cas’s thighs. “Don’t rush yourself, take your time.”

“So good,” Cas squeaked. “Feel’s so good.”

Dean let out a breathy laugh, “Yeah?”

Cas bit his lip and nodded, “Yeah.” Dean’s hands gripped Cas’s thighs as the boy clenched around him "You’re so big!” Cas gasped out a moan, his nails digging red crescents into Dean’s skin. “Oh, my _god_ , you’re _so_ big!”

Dean moaned, “I like you like this,” He laughed out breathily again, “You talk so much.”

“Oh,” Cas whimpered, dropping his head forward, “Oh my god.”

“So fucking hot, Cas,” Dean praised, “You’re almost there. It’s okay, take your time. You don’t need to rush.”

“You’re so _big_!” Cas’s mouth hung open as he panted.

“You’re doing so well, baby,” Dean cooed, “Doing so good for me.”

“Only — ah — for you,” Cas moaned out. “How much — How much more?”

“It’s okay, baby, just keep going slowly, you’re almost there.”

“Mh-hm,” Cas hummed. He gritted his teeth as he pushed himself farther down no Dean’s cock. Cas’s eyes snapped open to look into Dean’s as he bottomed out and a broken whine was pulled from his throat. “Oh!”

“Don’t move,” Dean instructed. Cas nodded, still not able to close his mouth. “Let yourself settle down.”

“Yeah,” Cas whimpered.

“It’s okay,” Dean soothed, rubbing his hands over Cas’s thighs and sides, “You’re doing so good, baby, so good.”

Cas was breathing hard and had trouble getting his words out. “Only for you.”

Dean smiled, “That’s right, so good, only for me. You’re so beautiful, angel. You’re my beautiful angel.” Cas smiled and nodded as Dean continued to say those sweet nothings that Cas just ate up. He loved when Dean would say things like he was saying now to him. And he loved when Dean called him baby or angel or babe. 

"God, Dean," Cas gasped, lifting himself up just slightly, testing how ready he was.

“Cas,” Dean whispered, his voice was hoarse, “Go at your own pace, okay? You move when you’re ready to.”

Cas nodded. “Okay.”

“Alright,” Dean breathed out, closing his eyes and gripping Cas’s thighs. Cas could tell he was having a hard time controlling himself.

“I think -” Cas had to catch his breath, “I think I’m going to move.”

Dean’s eyes opened, “Okay, just go at your own pace?”

“I-I know,” Cas stuttered. He closed his eyes and pushed himself up onto his knees. “Oh, my god!”

“Go slow, babe.”

“Shut up, Dean,” Cas gasped, throwing his head back as he sunk back down onto Dean’s cock. “Oh my god, _you’re so big_! Dean!”

“Cas-”

“ _Shut up, Dean_!” Cas ground out as he picked up his pace. He was fighting really hard not to come right on the spot; he wanted to let Dean be able to not have to do all the work every time they made love. Cas was focusing completely on letting Dean lay back and have the pleasure of just enjoying himself.

A string of curses left Dean’s lips as Cas started to pick himself up and fall back into Dean’s lap. “Fuck, Cas! You’re so _tight_ !” Cas couldn’t stop himself from repeating the same words over and over again: _Dean_ , _oh_ , _please_ , _yes_ , and _so big_. “Damnit Cas.” Dean’s voice could barely be heard by the boy through his haze of pleasure. “Are you getting close, angel?” Cas bit his lip and whimpered while nodding his head up and down vigorously. Dean’s mouth twitched up in the corner. “Go faster,” he said. Cas nodded and sped up — sitting up on his knees to the point where if Dean had been any smaller he would’ve slipped out of Cas — and all but slammed himself back down.

Dean expected Cas to scream or something; in no way was he prepared for what really happened: Cas’s head flew back with his mouth open and eye squeezed shut as his hands flew back to Dean’s thighs and gripped Dean almost painfully. He drew in a stuttering breath before raising himself up again repeated his motions, screaming this time. Dean guessed Cas had angled himself so his prostate was being hit each time he sunk down.

Cas had a hard time getting his words out when he finally spoke. It was hard for Dean to understand him, too, but it wasn't hard to guess what he was trying to ask: _how close are you?_ With the state Cas was in, Dean was about to lose himself.

“Fuck, Cas, just like that, I’m so close,” Dean stuttered.

“Yeah,” Cas slurred out. Dean looked up and saw Cas looking at him with a completely debauched expression and painfully arousing look in his eyes and it had him groaning out Cas’s name as he came. He felt the warm release of the boy spurt over his stomach and chest not even a second later. Dean’s hips thrust into Cas of their own accord, making him fall forward onto Dean. The boy whimpered into Dean’s neck and Dean could feel Cas’s cock trapped between them getting stroked with each buck of Dean’s hips.

"Fuck," Dean muttered, wrapping his arms around Cas.

“Dean,” Cas whispered almost inaudibly. He wasn’t strong enough to get up and let his oversensitive length breathe. The older man could tell the stimulation was getting to be too much and probably somewhat painful. “Nuh!”

“I got you,” Dean turned his head to kiss Cas’s forehead before he wrapped his arms around him and rolled onto his side, pulling out of Cas as well. He carefully laid the boy on his back and put his arm under his head. “You okay?”

Cas breathed hard, his eyes not able to stay open. “Yes.” His voice was completely wrecked. Dean smiled and pushed himself up to lean over Cas, just looking at his beautiful angel.

He was so fond of this boy. He didn’t know why. There were so many other people he was fond of and cared for, but it was different with Cas.

 _Love_.

Dean felt himself jerk in surprise. _Love?_ No, this isn’t love. Dean just cared for the boy. Very much. But it wasn’t love...

...Was it?

“Dean?” Cas whispered, looking up at Dean, his eyes glazed over with adoration. “Are you okay?”

The pirate nodded and leaned down to kiss Cas tenderly. “I’m more than okay,” he whispered against Cas’s lips, smiling at the warmth that flared inside him whenever he touched his angel.

“What time is it?” Cas asked.

“It’s about three in the morning,” Dean responded, memorizing Cas’s features.

Cas  sighed, closing his eyes all the way and smiling. “Good,” he hummed. “I’m exhausted.” Cas licked his lips as Dean chuckled, laying down on his side next to Cas, and moving his hand up to massage circles into Cas’s stomach. Cas inhaled quickly and moaned quietly. “That feels really good.”

Dean nodded, closing his own eyes in contentment. They stayed like that until Dean heard Cas’s light snores. The pirate pushed himself up again and studied his peaceful face.

“Cas…” Dean whispered, his heart pounded in his chest. “You’re making me rethink my entire life. You’re making me want to give up everything I’ve ever had…. Just for the chance to be able to wake up next to you every morning.” He paused for a second, not sure what to say.

Dean opted for nothing. He laid himself back down next to Cas and watched his profile before falling asleep with a full heart.

~  ~  ~

_February 17, 1963_

 

“Dean!” Cas yelled, waking the sleeping pirate up. He had to squint at the morning light. “I’m gonna be late again!”

Dean took a moment to register what Cas was saying. A second later he was up and getting dressed with Cas by his side doing the same. “Shit!”

“We fell asleep,” Cas said in a panicked voice.

“I know, I know! I’m so sorry!” Dean almost fell over trying to pull his drawers on. “Fuck!”

“What time even is it?” Cas asked, pulling a shirt from the overnight bag they’d grabbed on their way off the ship last night.

Dean looked up at the sky to judge where the sun was. “It looks like it’s about ten am.”

“No,” Cas groaned as he sat down to pull his shoes on.

“I’m so sorry, Cas,” Dean said pulling his pants up and buckling his belt. “Fuck! I shouldn’t have fallen asleep.”

Cas spared a second to look up at him, “It’s not your fault.”

“But it is,” Dean shook his head. “I should’ve woken you back up or carried you back to your own bed. I shouldn’t have fallen asleep.”

Cas stood up and gave Dean a quick kiss, “I don’t blame you,” he backed away, “I’ll see you tonight?”

Dean nodded, “Yeah. I’m sorry.” Cas shook his head before turning around and breaking out into a sprint.

“Go help Lisa,” he yelled over his shoulder. Dean nodded to no one in particular as he bent over and picked up the items they’d brought for their night in the woods; after he was sure he’d gotten everything, he  made his own way back to his ship, smiling a little to himself.

Despite making Cas be late - again, Dean had noticed Cas was running a little funny. He was probably blissfully sore from what they’d done early that morning, Dean concluded, laughing under his breath and feeling his chest swell with a sort of pride.

~  ~  ~

Cas ran as fast as he could; considering.

Every step resulted in a jolt of stinging pain. His thighs were sore from riding Dean, and his abdomen right above his groin was sensitive to the touch. Not to mention his throat was pretty dry and scratchy. 

The lights in his father’s study were on, hopefully meaning that his father was running late as well. Usually, his father would come wake him up at nine and have him get ready for his schooling until two in the afternoon, and then town council meetings until six. This was the routine every day, except for Saturday’s and Sunday’s. His uncle had convinced his father to keep those day’s left open.

Cas came to a stop upon reaching the back entrance that lead through the kitchens into the den and from there he could make his way up to his room, hopefully without being noticed. But no such luck. As soon as he entered the den, his father called his name. “Castiel.” His voice was harsh and cutting. “Where have you been?”

“I’m sorry father,” Cas turned to face his father, not meeting his eyes. “I woke up early and went to the library. I lost track of time again.”

“Castiel,” His father’s voice was disapproving. “You know I don’t tolerate lying.” Cas heard his father get up and walk over to him. He could smell the soap he used: pine. Cas hated the smell.

“I’m not lying, father,” Cas said in a small voice. He closed his eyes and braced himself for the beating he was sure to get. But it didn’t come and Cas felt himself let out a thankful breath.

His father scoffed, “Right.” Michael walked past him and to the fireplace. “Do you take me for a fool?”

Cas shook his head, “No, father.” He heard his father grab one of the fire pokers and come to stand behind his son.

“Well.” Michael let out a dry laugh. “You must think I’m a fool,” His father laughed again; but angrily this time. “Since you keep lying to me!” He brought the poker down on Cas’s back.

Cas’s scream was heard throughout the house, "I'm sorry!"

"You _keep_ lying to me!” More hits against Cas’s back. The boy was on the floor and trying to keep his sobs in. “So you must think I’m a fool!” Michael punctuated each word with a violent whip on his son’s back.

“I’m so sorry father!” Cas sobbed, his arms shaking from trying to keep himself up. “I don’t know what you want me to say!” He heard his father laugh once again before a sharp, quick pain shot out from the back his head. His father had his hand in his hair and was forcing Cas to look him in the eyes.

“It’s simple, Castiel,” His father smiled bitterly. “I don’t want you to say anything.” Cas sobbed, making his father sneer and let go of him. Michael stood up and threw the poker next to Cas, who had collapsed. The loud clang made Cas jerk away from it and sob loudly again. Cas brought his hand up to his mouth to stifle the noises. "I want you to do as I tell you and quit screwing everything up!" 

"I'm sorry," Cas wheezed, his back starting to go numb. He heard his father as Michael paced the room angrily for minutes until the older man started to shout at Cas again.

“You were supposed to be my pawn in changing  _everything_ !” Michael stopped himself in his tracks, glaring at Cas for the longest time before walking over to him again. “But no, you had to be late the one morning which would've changed everything! Dean Winchester would be dead by now and I would be a hero! But you were late, you pathetic piece of scum! N ow Crowley’s daughter has been wedded to another!” Michael kicked his son in the ribs repeatedly, making Cas yell and gasp for mercy. “I’m stuck here, doing whatever Crowley wants because he wasted his time in coming here to inspect you when you didn't even bother to show up! I would've been part of Crowley's royal court! But you!—” _Kick._ "—were at the—" _Kick._ "—goddamn library!" 

“Please father, I’m sorry! I’ll do better!”

Michael scoffed. “There is nothing you can do to fix anything now.” He snarled and kicked Cas again before storming out.

Cas cried, “Please." He was not able to breathe well from the air being kicked out of him. There wasn't enough oxygen getting to his brain. He struggled to get up, but couldn’t. His body was too weak with pain, his brain was starved, and his vision was going blurry . “I’m sorry!” He cried before giving up and passing out on the floor, once more.

~  ~  ~

“Will you be okay?” Dean asked a teary-eyed Lisa. They had made their way to the constable’s station to get Ben back. They would need a document from the Chief before they could go to the orphanage and pick Ben up. Lisa nodded her head vigorously. Dean took her hand in his and pushed the station. The person at the desk was dressed in navy blue - a constable off duty - and his eyes flicked up lazily to see who had entered before going back to the book he was reading only to shoot back up to look at Dean Winchester. Dean _“The Righteous Man”_ Winchester of the Impala 67.

“I need to see Constable Uriel,” He announced.

“Now,” Lisa added, stepping in front of Dean and slamming her fist on the desk. “He took my son from me.”

The officer at the desk rolled his eyes at Lisa. “Look whore, you’ve got no job, no money, and no house. There’s no way you’d be able to give Ben the care and attention he needs.”

Dean could see Lisa tense up so he intervened. “No,” he put his hand on Lisa’s shoulder and pulled her back. “She’s got money, she’s got a job, and she’s got a home.”

“Oh, yeah?” The officer challenged, “Where?”

Dean smirked and replied without missing a beat, “On the Impala 67.”

The officer paled. “What?” His eyes went to Lisa, “You’re a pirate now?”

Lisa sneered, “Get me Uriel now!”

“I’d do as she says, buddy,” Dean leaned onto the desk, “She’s a pirate. 

The officer let out a nervous laugh before stumbling out of his seat and all but running to Uriel’s office. They came out together a minute later, Uriel looking unaffected.

“Lisa,” he started. “Drop this nonsense. You’re not a pirate. You’re a whore.” His eyes scanned her body hungrily. “I’ll even buy you right now.”

“I’d be careful if I were you, Uriel.” Dean nodded at Lisa. “She’s so close to taking out a Demon Deal with me. They’re real cheap for people who work for me. Almost _priceless_.” Dean smirked.

“You said yourself,” Lisa sneered, “I’ve _‘got no money.’_ But it’s still enough to take out a Demon Deal on you.”

Uriel’s eyes narrowed and he nodded curtly saying, “Fine.” He walked back to his office and came back a moment later with the documents Dean and Lisa needed to get Ben back. Lisa snatched them and headed out the door.

“Thank you, gentlemen,” Dean said, only to rub salt in the wounds. “I guess I _won’t_ be seeing you around.” He winked at them as he followed Lisa out.

Lisa said once he’d caught up with her, “Thank you, Dean. That was brilliant in there - saying I was part of your crew. Thank you so much. You have no idea how much this means to me. I’ll never ask anything else of you; ever. I promise. You’ll never have to hear from Ben and I again. We’ll disappear.”

Dean nodded, “Well,” he said. “I was actually thinking that maybe you two could actually come with me on the Impala.” Lisa’s stumbled when Dean finished.

“Dean, I—”

“My crew is honest and good people. You wouldn’t have to worry about anything ever again. Ben would be family and he’d get all the love and attention he could ever want.” Dean finished as they arrived outside the orphanage.

“I don’t know…”

Dean stepped up to her and took her hands in his, lowering his voice to speak, “I can protect you two. You’ll never have to sell yourself again.”

"I..." Lisa took a moment to look into Dean’s eyes before she nodded. “Thank you.” Tears falling from her eyes. Happy tears. Dean grinned as he took Lisa’s hand and they walked in together and got Ben.

~  ~  ~

Cas limped himself to Dean’s ship that night. His back was in bad shape and his head was fuzzy. As soon as Dean saw him, he picked the boy up and took him to Gilda.

“What happened?” She asked, her voice calm but her eyes wide with surprise. “Were you mauled by a lion?”

“My father—”

“Your _father_ did this to you?!” Dean exploded, almost crushing Cas’s hand. “Michael did this?!”

“Dean—”

“I swear to God I’m gonna — _Fuck_! I’m gonna—”

“Dean, calm down,” Gilda tried, pulling off Cas's shirt.

“You’re telling me to calm down?!” Dean yelled. He pounded his fist on the table Cas was on, rattling the wood and sending vibrations throughout Cas’s body. “I'm going to rip his lungs out! I’m going to _end_ Michael!”

“Dean, you need to go. I can’t have you stressing Cas out right now,” Gilda said, looking at him pleadingly.

“What?! No! I’m not leaving him!”

“I’m sorry Dean,” Gilda jerked her head towards the door. “Benny, Sam.” Dean yelled and struggled as Benny and Sam dragged him out.

“Am I in that bad of condition?” Cas asked.

“No,” Gilda said immediately, helping Cas to lay onto his stomach. “But Dean tends to get rather worked up; especially when it involved the people he cares about. You’ll be fine. You just need a few minor stitches in your back, and I need to heal your chest. Your rib was bruised”

“What do you mean?” Cas asked, wincing. “You have to ‘heal’ me?”

“Dean didn’t tell you?” Gilda asked, “I’m a fairy.”

“Oh,” Cas winced again. “Thank you,” he ground out, squeezing his eyes shut when he felt something sharp dig into his back.

“Why did your father do this?” She asked a moment later.

“Dean and I overslept and I was late to his schooling,” Cas explained. He gripped the edge of the table and bit down to combat the pain he felt in his back.

“Your father sounds like an asshole,” Gilda stated. Cas let out a huff of a laugh.

“I hate him.”

“My father used to beat me, too,” She said as she walked away from Cas to grab something. “It’s part of the reason why I joined Dean. That and Charlie.”

“I’m sorry,” Cas turned his head to look at her out of the corner of his eye. She smiled warmly while she worked.

“Thank you. I’m sorry about your father, as well, Cas.” Gilda turned to drop the needle she was using and grabbed some bandages. “No one should have to endure this.”

Cas sighed as he felt a cool, numbing cream be spread over his wounds. “It’s okay.”

Gilda stopped to look Cas in the eyes, “Don’t tell yourself that.”

“It’s just a part of life,” Cas shook his head. Gilda furrowed her eyebrows.

“No,” She whispered, “It’s not.” Cas wasn’t sure how to respond and her gaze was so intense. “Don’t let yourself think that because of the way your father is — abusive — that you have to sit back and endure it. You don’t.”

Cas could feel more tears slip out of his eyes. “I have to.”

Gilda smiled sadly and rubbed more cream on Cas’s back before closing her eyes and mumbling some words. Cas felt his back become warm and the pain went away. “I’ve used a spell to make your cuts heal as two times faster than normal, so it should be about three days until you can really be able to move without any pain,” Gilda said, opening her eyes and looking at Cas again. She nudged Cas to flip onto his back and he followed through.  “I wish Dean would just take you with us when we depart again.”

“Me too.”

Cas saw Gilda smiled. “I think you’d be a great pirate.” 

It was Cas’s turn to smile now. “Thank you. But I’m just me; the only thing I know how to do is read and observe council meetings. I don’t blame Dean for not taking me with him.”

Gilda’s brows drew together again, “That’s not why he doesn’t take you with us.”

“What do you mean?”

“He thinks he’s protecting you from a life of crime, uncertainty, death, et cetera,” She explained. “Dean doesn’t want you to wake up a year from now and regret joining him. He worries about that with everyone he takes into his crew. But he’s much more adamant about you when it comes to the subject of bringing you along.”

Cas felt a soothing warmth spread through him. “Really?”

“Yes; he really cares about you.”

“I really care about him, too.” Cas closed his eyes. His back was numb and the only pain he could feel was in his ribs.

“Stay still,” Gilda said and Cas felt the a more intense warmth spread through his chest. “Can you sit up?” Gilda asked. Cas nodded while she helped him to swing his legs over the table and to sit facing her. “Arms up.” Cas did as he was told, looking at her hands as she recited another spell.

“Gilda!” Cas heard Dean scream from outside. She only rolled her eyes in response.

“How does your chest feel?” She asked, looking into Cas’s eyes as she used her hands to press against where his father had hit him.

“No pain whatsoever,” Cas smiled, “Thank you, Gilda.”

She smiled back at him. “Of course.”

“ _Gilda_!” Dean yelled again.

“Oh for fucks sake I’m going to let him back in.” Gilda threw her hands up and walked out. Dean came running in a second later, breathing hard and eyes wide.

“Are you okay?” He asked immediately and came to stand in front of Cas, between his knees. Cas nodded.

“I’m fine. My ribs are all good and my back is on the fast track to being healed up.”

“Oh,” Dean breathed out, stepping closer to Cas. Neither of them spoke for a long while; Dean just traced over Cas’s chest and rubbed his back in a way that Cas couldn’t feel. “I’m sorry.” Dean sounded broken. “I should’ve never fell asleep. I’m so stupid! I should’ve taken you back.”

Cas shook his head, “Shut up, Dean. This isn’t your fault.”

“I just want to protect you,” Dean whispered, “But I fucked up and now you’re hurt.”

Cas shook his head again and brought his hand up to cup Dean’s face. “This isn’t your fault. It’s no one’s fault but my father’s. Okay?” Dean closed his eyes and leaned into Cas’s touches. “Plus, I’m not that hurt. Gilda used her magic on me.” Dean smiled and nodded before leaning in and kissing Cas tenderly; he kissed Cas as if he kissed him too hard he’d break the boy. Cas pulled Dean with him as he laid himself down, never breaking the kiss. Dean rubbed along Cas’s side with a hand while the other hitched Cas's leg up over his hip. Cas smiled into his kiss and moved his hands to undo Dean’s pants. But the pirates hands stopped him.

“I don’t know, Cas,” Dean breathed out.

Cas whimpered, “Please.”

“I don’t want to hurt you more,” Dean argued.

“I can’t feel my back,” Cas said. He grabbed the hand Dean had on his side and pushed it into his groin while taking the pirates other hand and bringing it to his chest.

Dean tried to protest further, but his hands betrayed him. They moved against Cas’s body in slow strokes. Cas reacted loudly, knowing Dean would break even faster with vocality. “We don’t have any oil,” Dean groaned. Cas blushed and reached into his pocket.

“I brought some.”

Dean felt his resolve crumble. “Fuck.”

“I’ll be fine,” Cas whined, again reaching to undo Dean’s pants.

Dean groaned before he nodded, “Okay, but we’re doing this gently.”

“Whatever Dean, just _please_ ,” Cas gasped. Dean let go of the boy’s hands and undid Cas’s slacks, pulling them off in a swift motion along with his drawers. Cas bent his knees and opened his thighs eagerly. Dean oiled two of his fingers, reaching between their bodies to circle his finger around Cas’s rim and in turn making the boy squirm. He pushed his digits in and crooked them in just the right way that made Cas’s hands shoot up to beside his head, gripping the edge of the table.

Dean pumped his fingers into Cas for several minutes, adding more at just the right time to make Cas’s legs shake and his breath come out in stuttering gasps.

“Oh, Dean, please!” Cas begged his voice sounding like a sob. Dean pulled his fingers out and undid his pants, pushing them down enough to get to his own manhood.

Cas moaned and let one of his hands come down to stroke his own leaking cock. Dean put his hands on the table next to Cas’s hips and pushed in. Cas whimpered and stroked himself faster as Dean began to thrust into him.

“You like touching yourself,” Dean grunted.

"Yes," Cas whined, moving his hips to meet Dean's thrusts.

"You'll come faster that way," Dean pointed out. Cas whimpered pathetically and stopped stroking his cock. His hand went back to grip the edge of the table hard.

“Dean,” Cas whined, his thighs quivering and opening wider. “Faster!” Dean kept his pace the same. Right now was not the time for a rough quickie. He knew Cas wanted it, but he wasn’t going to allow that. The pirate looked down at Cas’s cock. He was sure the small length was aching painfully to be touched again.

"Everyone is outside, you know," Dean whispered, leaning over to kiss Cas's narrow chest.

“Ah!” Cas whimpered loudly, his eyes screwed shut. “Oh, Dean.”

“Sh,” Dean grunted, “You don’t want everyone to hear us do you?”

Cas groaned in frustration, at the point of not even caring if his own father was about to walk in. He just wanted Dean to fuck him. “D-don’t care. Faster! Harder!” Cas begged.

“I told you this was going to be gentle,” Dean denied the boy his pleas. Cas gasped loudly and arched his back. He moaned loud enough to wake up the entire ship and thrashed his head from side to side. Dean slowed down further, making Cas gasp and babble out incoherent words.

"De-e-ean!" Cas moaned brokenly. Dean felt himself getting close to his own release; he quickened his hips only slightly, but it was enough to make Cas gasp loudly and push himself onto his elbows to look into Dean’s eyes.

“You want to come so bad, don’t you,” Dean said it like it was a statement and not a question. With the state Cas was in — eyes glazed over and his mouth slack with whimpers and whines falling out one after the other — Dean didn’t even have to phrase it as anything but a statement. But Cas still nodded his head. Dean angled his hips up — just slightly — and almost came at the sound Cas let out: a cross between a whimper and a yelp. He made sure to keep just brushing past Cas’s prostate in order to keep that noise falling from Cas’s pink and plump lips.

Cas panted in order to catch his breath enough to speak, “Ple-please.”

Dean inhaled sharply, “Not yet.” Cas cried out and let himself drop back onto his back with his arms up gripping the edge of the table again. His legs fell even more open and his thighs trembled violently.

Dean’s eyes raked hungrily down Cas’s flushed body to stop at his cock. There was a steady stream of precome leaking onto Cas’s stomach. The boy Dean was so fond of was a sight to behold like this: legs trembling, mouth open, eyes squeezed shut, and his small length aching to come. Cas sobbed out a whine. Dean took pity on the boy and slammed into him, hitting his prostate and making Cas scream out Dean’s name as he came, pulling Dean over the edge with him.

The older man looked up at Cas and grabbed his hands. He brought them to his mouth and kissed the palms gingerly. Cas smiled at him and tried to sit up, hissing when he was met with a dull ache in his back. Dean stood up and grabbed Cas’s clothes after pulling his own trousers back up. He got Cas back into the articles of clothing before helping Cas up into a sitting position.

They kissed sloppily, just pressing their lips together for a few seconds before pulling back for air. Dean’s hands immediately went to Cas’s hips and Cas’s hands went to Dean’s hair.

“Did you have to do that in here?” Gilda barged in, glaring at them. Cas blushed and pushed his face into Dean’s neck.

“Sorry,” Dean said, totally not meaning it, “Duty called.”

“Right. And Cas, your back?” She put her hands on her hips. “No extraneous activities!”

“If it counts for anything, I did most of the work,” Dean offered.

“Oh my gods, Dean, I did not need to know that.”

“You’re his doctor,” Dean joked. “I thought you’d be happy he wasn’t doing any over-the-top activities.”

Gilda sighed, “No, Dean, no.”

“Well-”

“Get out,” Gilda said. “I need to clean up.”

Dean laughed and helped Cas up off the table and onto the floor. He took Cas’s hand in his own and grabbed the smaller boy’s shirt on the way out; Cas pulled it over his head just as they stepped into the hallways below deck. Charlie, Benny, Sam, and a blonde woman were outside talking. They looked at Dean and Cas as the two walked into their group.

“Aye?” Dean asked, keeping Cas close to his side.

“My ears are ringing,” the blonde woman said. Charlie hit her arm.

“Jo!” She scolded. Cas buried his face in Dean’s shirt to hide the blush that he was sure made him look like a tomato.

“That was a compliment,” Jo said as if it were obvious, making Cas blush harder. “Kid’s got pipes.”

“Don’t I know it,” Dean said, making the group laugh and Cas bury his face farther into Dean. The boy tuned the four crew members out and inhaled Dean’s scent. You would think he’d smell like fish or salt — something oceany. And while that was somewhat true, Dean smelled more like the leather trousers he always wore and wood after it had rained. It was something Cas found very pleasant.

Dean started to pull him along down the hall. Cas let himself be guided onto the main deck of the Impala and then into Dean’s cabin. He walked over and crawled onto Dean’s bed, stretching himself out and grunting at the slight pain it caused him.

“Did I hurt you, Cas?” Dean asked, coming to sit down between Cas’s legs and rubbing them soothingly.

“No,” Cas sighed. “It was perfect.”

“Won’t you be sore tomorrow, though?”

Cas cracked an eye at him, “I’ll be sore alright. But not from you.”

Dean frowned at him and shifted to lay down on his stomach, using Cas’s belly as a pillow. “I have an alarm set for tomorrow.”

“That’s good,” Cas mumbled, pushing his hands through Dean’s hair and smiling at the sighs Dean exhaled through his nose.

“You can fall asleep if you want to, babe.”

“Mhm,” Cas hummed, his hands coming to a stop as he drifted off to sleep to the pleasant feeling of Dean’s heavy head on his stomach and his hands on his sides, holding him protectively.


	6. Chapter Six

**Summary for the Chapter:**

> Cas's birthday comes up and Dean's plans for the day are finally revealed. Plus, a little something else Dean had planned comes into light.

Chapter Six

_February 21, 1693_

 

Just like Dean’s first week back, the second one — the one leading up to Cas’s nineteenth birthday — went by faster than either of them would’ve liked.

Cas’s back healed up nicely. Gilda had said it was almost too quickly; even for one of her spells. Neither Dean or Cas were complaining though. Cas’s self-healing abilities just made it easier for them to be intimate in the way they both wanted.

“ _Castiel_ ,” Michael said, stepping in front of his son and looking at him with poorly hidden disappointment. His features were highlighted by the lamp behind Castiel. The sun had set an hour ago and it was the only thing keeping the room from being pitch black.

“Yes?”

“I expect you to have your work done by the time I get back and have the next articles started.”

Cas nodded shallowly, “Yes, father.”

“Don’t disappoint me.”

“Yes,” Cas said, trying not look his father in the face. “I understand, father.”

There was an unspoken promise that Michael left with Cas that if he didn’t finish his work, he’d be punished… And Cas knew what Michael’s punishments meant.

When he was seven, his father had locked him in his room and starved him for two weeks with minimal water because he’d wandered off one day in the market when Michael was teaching him about how their town worked. Cas was drawn to the harbor and the ships docked there; he didn’t know it then, but that was himself saying he wanted to get away.

But what Michael didn’t know was that Cas had already finished all his work, and started on the next articles. He stayed up for the past two nights getting it all done.

“Good bye,” Michael said, leading the staff hands carrying his suitcases outside to his carriage.

“Bye,” Cas whispered. He stood there, looking at the front door and waited. When the staff scurried back into the house, Cas felt himself break out into a smile. He raced upstairs and packed a bag for his time with Dean, too happy to really check what he was throwing in there. All he cared about was getting to Dean and seeing what he had had planned for tomorrow.

“Castiel,” His mother called. “Did your father leave?”

“Yes,” Cas called back, not wanting to have to engage in conversation with her at the moment. “I’m going to the library to study, mother.”

“Yes, Castiel,” his mother’s voice became quiet as Cas heard a door shut. It was no secret his mother was unfaithful to his father. She’d been sleeping with the help for years; since Cas was at least eight and he’d walked in on the former cook with his mom on his lap and the his hands on her breasts.

Of course, he didn’t understand at the time what was going on; so he just walked away and tried to forget about it.

Cas grabbed his bag and rushed down the stairs, flinging the door open to reveal his uncle.

“What’s up Castiel?” He smiled, pushing past him into the house. “I was thinking we could do something tomorrow for your birthday?”

Cas had to silence a groan that was threatening to spill out. “Actually, I already have plans.”

“What?”

“Dean and I—”

“Oh, I see.” Gabe shook his head. “You’d rather hang out with _Dangling Dick Dean_ than your ol’ uncle Gabe. I see how it is.”

Cas blushed bright red at the nickname and shuffled from foot to foot. “You can... Come with me... I guess...”

Gabe grinned. “Let’s get going, then?”

Begrudgingly Cas opened the front door and ushered Gabe out, leading him to the harbor.

~  ~  ~

Dean was smiling when he saw them and immediately picked Cas up and spun him in his arms, kissing him deeply.  

“C’mon guys,” Gabe groaned loudly. “Let’s try and be at least a little professional.”

Dean looked at him with an amused look. “You do understand you’re about to set foot on a pirate ship, right? There’s nothing “professional” that goes on on my ship. Well, except Benny’s cooking.”

Gabe looked at him with hopefully eyes, “Does he do desserts?”

Dean nodded, “Well, aye; of course.”

“Let’s go!” Gabe ushered the couple up the dock stairs and to the gap between the boat and the docks.

“Alright, here’s how you get on,” Dean said, letting go of Cas to let him demonstrate.

“Shit, man!” Gabe yelled, rushing forward as he watched Cas swing from the docks onto the ship. “You let him do that? He’s only a kid!”

“Well, is he really, though?” Dean smirked as he handed the rope to Gabe, who took it, but looked very nervous. Dean laughed quietly before grabbing the rope back and pulling Gabe into his side to swing them onto the boat without warning. Gabe yelled in panic and clung to Dean.

When they landed on the deck a moment later, Gabe immediately separated from the pirate. “What the hell, Winchester?!” Dean just smiled and collected Cas into his side.

“You want a tour?” He asked Gabe while kissing the top of Cas’s head.

“No,” Gabe grumbled out. “I want something sweet.”

Dean smiled again before taking Cas’s hand and leading them to the mess. “In here is where we eat,” Dean said. It was a rather large room. All of his crew could fit in here and eat with room to spare.

“What the-?” Gabe gaped, looking around. “Damn, your ship really is massive.”

“Absolutely,” Dean answered, “My brother, Benny and I built a lot of it. The mess used to be six times smaller than this. But, you know,” Dean winked at Cas, “I’ve always been pretty handy with my fingers.” Cas blushed and hid his face from Gabe in Dean’s coat.

“Really?” Gabe asked, very clearly too interested to register what Dean had really just said.

“Yeah,” Dean swept his hand out, “The whole ship actually used to be about ten times smaller than when I bought it. My cabin was just a small cot and a chair at first, but Sam and I expanded it. Plus with all the money we make from contracts, we don’t need to worry about shortages of anything. Plus the occasional pillage—”

“Dean!” All three men looked over to see where the voice came from. Cas remembered him as Ash.

“Aye?” Dean responded.

“I think I finally figured out the canons,” Ash announced joyously. “May I show you the plans?”

“Aye,” Dean nodded. He turned to Cas. “Will you and Gabe be okay to talk to Benny without me. You can ask him to make you whatever you want.”

Cas smiled and nodded, “Yeah, I don’t see why not.”

Dean smiled back, “Perfect, I’ll send Sam and Charlie in here, too.”

“Okay,” Cas said. He smiled wider at Dean as they pecked and Dean left. Cas started to walk towards Benny, who caught his eye at the counter where the warming trays of leftover dinner were and smiled, but Gabe stopped him.

“So,” He started, “About Dean...”

“What?” Cas’s heart started to drop. “You don’t like him?”

“No, Cas, he's swell. But...”

“What?”

“He loves you,” Gabe said plainly. “Maybe he doesn’t know it himself, but it’s really _disgustingly_ obvious.”

Cas shook his head, “What are you talking about? We just enjoy each other’s company.”

“No.” Gabe looked straight into Cas’s eyes. “He loves you.” Cas wasn’t able to respond. He didn’t know what to do with this information. Gabe lowered his voice. “Do you love him?”

“I...” He was at a loss for words. Cas knew the answer though. He’d known it the moment Dean left all those months ago.

Gabe laughed and shook his head. “You’ll figure it out.” He looked at Cas with a glint in his eye; as if he knew something about Dean and Cas that Cas didn’t. After a slap on the back, Gabe left his nephew to head over to Benny. Cas stood by himself in the mess hall, thinking about what Gabe had said.

Dean loved him? How could Gabe be so sure? Dean never said anything to Cas before about it. What was he supposed to do with this information? What did Gabe know that Cas didn’t?

He shook his head and looked over to find Gabe, but he was gone. Cas wasn’t majorly worried, but he was a little. Gabe did have a reputation for getting himself into trouble.

“Cas!” Charlie squealed, running over to hug him. “Happy early birthday!” Cas smiled at Charlie before he looked behind her to see Sam and Gilda approaching them.

“Hello, Sam, Gilda.”

“Hey,” Sam responded back, smiling as well.

“Happy birthday, Cas,” Gilda gave him a quick hug.

Sam walked over and gave Cas a hug, too. “Happy birthday. Nineteen, right?”

“Yeah,” Cas smiled at the three pirates. In the time that Cas was on board, the nights where Dean and him didn’t have sex, they spent around his ship talking with the people who were still up. Most often it was the same group: Charlie, Gilda, Sam, Benny, and sometimes Kevin or Ash. “Thank you for the birthday wishes.”

“Are you hungry?” Charlie asked. Cas felt Charlie sling her arm over his shoulders, something she was too short to be doing, but he didn’t mind. She pulled Cas forward towards Benny’s station.

“Not particularly, but if there’s any of Benny’s peach cobbler left I’d love to have some?”

“You betcha I do,” Benny handed him a plate with a slice of delicious looking cobbler and a fork.

“Thank you, Benny,” Cas smiled, “Where did Gabe go?”

“He’s in back digging through the hard candy I got.” Benny smiled.

“I should’ve known,” Cas sighed before sitting down at a table with Charlie, Gilda, and Sam following suit; Benny came to sit down not much later with a pitcher of what was called “ _Benny’s Famous Grog_ ” by Sam and Charlie.

“Diluted rum, lad,” Benny explained.

“Diluted with what?” Cas asked.

“Brown sugar and spices,” Gilda took a sip of Charlie’s and nodded her head. “It’s good. But not for me.”

“That’s because you’re from fairy-kin,” Charlie laughed. “You don’t like anything that’s fun.”

“I like _you._ ” Gilda kissed Charlie’s forehead. Cas smiled at the exchange.

“You want some?” Benny offered Cas his cup.

Cas hesitated before shaking his head and saying, “I’m okay, thank you.”

“Alright,” Benny laughed, “I’ll try not to take offense.” He joked. Cas laughed quietly as everyone began to talk over each other and drink the grog.

The group was so invested in talking no one but Cas noticed when Gabe came back out with a plate of candy and sat down next to his nephew; he slid into the conversation easily and seamlessly. It was like he belonged with these people.

Gabe was thoroughly invested in the conversation and was asking questions about life as a pirate. And the others talked with animated faces and wild arm movements, almost slapping each other in the face sometimes.

“Everyone having a good time?” Cas heard Dean’s deep, rich voice. Nods and sounds of agreements were heard among the pirates at the table along with an enthusiastic nod from Gabe. Dean caught Cas's eye and jerked his head toward the exit.

“Excuse me,” Cas said, standing up with his plate to take it to the sink.

“Don’t worry, I got it,” Benny said, grabbing it from Cas and setting it back down. “You get to your _thing_.”

“Thank you, Benny,” Cas mumbled shyly and blushed, walking over to Dean and leaning into his side.

“Well, if you’ll excuse us, Cas and I have some business to attend to,” Dean said, smiling and turning himself and Cas away from the people at the table.

“Of course,” Sam smirked, “Captain.” Dean rolled his eyes and pulled Cas with him out of the mess, wrapping his arm around the smaller of the two to keep him warm.

“I think Gabe fits in really well with your mates,” Cas said, looking up at Dean.

“I’m glad,” Dean replied. “I really want him to like me, if I’m being square.”

Cas bit his lip as he spoke with hesitancy, “He _does_ like you.” Dean heard the layer of emotion in Cas’s words.

“What?” Dean asked, opening the door to the cabins. “What’d he say? Does he not actually like me?”

Cas shook his head, “No, that’s not it.” He walked into the hallway with Dean following him closely until they got into Dean’s room and he headed over to the desk, leaning back against it. “He just... Said some things to me... About you.”

Dean eyed Cas warily, “What things?”

“Nothing bad, I promise.”

“That's good to hear... What things?” Dean persisted, pulling up a chair in front of Cas. “You can sit on my desk.”

Cas hopped up and allowed Dean to scoot between his legs. He rested his hands on Cas’s thighs as Cas spoke. “It was nothing, Dean.” Cas shook his head. He didn’t want to jeopardize his relationship with Dean.

“Angel,” Dean said softly, standing up to push some of the papers on his desk to the side. “You know you can tell me, right?”

Cas nodded, “I know.” He bit his lip and spread his legs farther apart while contemplating the idea of asking Dean about what Gabe had said. Finally, Cas shook his head. “It’s not important. He was just teasing me.”

Dean eyed him skeptically. “Okay,” He said; Cas knew Dean wasn't convinced, but he also knew Dean wasn’t going to force him to say anything. “Well, back to the task as hand?”

Cas smiled. “Scoot back,” he said. Dean did as he was told, watching Cas sink to his knees and pull at the knot of Dean’s pants, letting out a frustrated groan when he wasn’t able to undo them and had to sit back to let Dean work the knot out.

“Little eager, aren’t we?” Dean teased, immediately shutting his mouth when Cas freed his length, sloppily and slowly licking from his base to his tip several times. “That’s...” he trailed off.

Cas smiled, kissing around the girth before taking the head into his mouth. He flicked his tongue across Dean’s slit, making the man hiss and a bead of precome to bead up. Dean groaned as Cas wrapped his hands around his shaft, pumping them to a quick rhythm. Cas loved every sound that slipped from the man's lips and sped up his pace. He felt strong hands come to run through his hair as Dean grunted.

“Cas.” Dean let his eyes drift closed. Cas looked up at him and watched his face until the pirates eyes snapped open again. His hand fisted itself in Cas’s dark locks. Dean’s lips twitched up in a smile as he moaned. “I don’t know how you do it, but I can’t seem to control myself with your mouth doing the things it does to me. I hate it.”

Cas giggled as he pulled off Dean. “I take that as a compliment,” he said, kissing around the head of Dean's cock. The older man groaned, looking down at Cas with hooded eyes.

“You know it wasn’t meant as anything else,” Dean laughed huskily, lightly scraping his nails across Cas’s scalp.

“Mh,” the younger boy moaned. “I like it when you do that.”

“Run my hand through your hair?” Dean asked, raising an eyebrow. Cas nodded, smiling as he took as much as Dean as he could into his mouth, only using one of his hands to move up and down along Dean’s shaft. He rested the other on Dean’s leg; digging his fingers into the meat of the man's thigh as he slowly took more and more of Dean’s cock into his mouth, he gagged when he felt the head hit the back of his throat.

“Don’t choke yourself,” Dean said, sitting up and pulling Cas off of himself. The boy coughed and had to wipe some spit dripping from his chin. Dean tried to pull Cas onto his feet, but Cas wasn’t having any of it.

“Sh,” Cas hissed, pushing Dean back into his seat. “I’m not a child.” He took Dean into his mouth again, bobbing his head and pumping the hand he had around Dean’s shaft while gripping Dean’s thigh with the other; hard enough to bruise someone who wasn’t as strong as Dean.

“You look so fucking amazing doing that,” Dean said, his voice thick with arousal. Cas looked up at Dean through his lashes and moved the hand he had on Dean’s thigh to his own clothed erection. He palmed himself furiously, whining around Dean’s shaft.

Dean let out a breathy laugh and tilted his head back and fisted his hand in Cas’s hair, grunting out Cas’s name as he came a minute or so later. He smiled as he tucked himself away and pulled Cas up to his feet. “On the desk,” He said, helping Cas to hop back up. Dean pulled the chair closer and sat back down in it, settling himself comfortably between Cas’s legs again. He looked up at Cas, watching the boy's face closely as he slid his hand over the hardness in Cas's trousers. Cas let out a small moan, putting his hand over Dean's and pushing down. Dean took Cas's wrists in his hands and put them flat on the table. “I got you,” Dean said quietly.

Cas whined quietly as he did as he was told, watching Dean's hand intently. “Dean, please... Please don't tease me.”

Dean smiled and said, “Since you asked so nicely.” He made quick work of undoing Cas's trousers and quickly swallowed the boy's length down. Cas gasped, moving his hands to grip Dean’s hair firmly for leverage. He closed his eyes as Dean's tongue flattened against the underside of his cock — just the way Dean knew he liked — and threw his head back. Dean hollowed out his cheeks gently and flicked his tongue across Cas’s slit a few times.

Dean was determined to make his angel feel as amazing as possible. He wanted to show Cas how much he treasured him. Dean hummed around his angel and pushed his hands under the boy’s shirt, running his hands over Cas’s sensitive nipples. He pinched and pulled on them before massaging his thumbs over them.

Cas tightened his hands in Dean’s hair and pushed his chest into the pirate’s hands. “Dean,” he squeaked, letting the older man know that he was close. His hands were tugging roughly at his hair and his hips were starting to thrust into Dean’s mouth at a uncoordinated pace. Dean closed his eyes and removed his hands from Cas’s shirt, continuing at his pleasant pace until Cas was doubling over and holding Dean’s head down. He cried out loudly as he came, "Dean!" His hips stuttered to a stop before he breathed deeply and laid back on Dean’s desk, removing his hands from Dean’s hair and letting them fall down next to his head.

Dean pulled off and came up for a kiss, pushing Cas back into his pants and drawers, buttoning them up. "You alright, angel?"

“Bed,” Cas said breathlessly, doing his part by wrapping his legs around Dean's hips and his arms around the man’s shoulders. Dean picked him up and carried him over to the bed, laying down with Cas on top of him. The two stayed like that; not needing to say anything, just listening to the other’s breathing.

“We don’t have to get up early tomorrow,” Dean whispered, trailing his hands up and down Cas’s back.

Cas sighed and buried his face into Dean’s neck, again, breathing in his wonderful scent. “I know.”

“Do you want to know what I have planned for tomorrow?” Dean asked.

“Yeah,” Cas sighed happily, nuzzling Dean’s neck.

Dean started, “I’ve found a place for us on the other side of the woods where we can spend the day together doing whatever pleases us. I’ve had Benny make pie and cobbler for dessert when we get back. We’ll do lunch there. For breakfast, I was thinking we’d stay here and let everyone give you the presents they got—”

“People got presents for me?” Cas asked, pushing himself up to look at Dean, who smiled at him.

“Aye, they love you.”

Cas leaned back down into Dean’s neck and smiled. “That’s sweet.” He closed his eyes again. “After that?”

“After that, we’d head out and spend the day by the lake. Cuddling, swimming, talking... _fucking_... et cetera.”

Cas giggled and kissed Dean’s neck. “Sounds perfect.”

“There’s one more thing I want to try, but that's for when we get back tomorrow night. And only if you want to try it.”

“What is it?”

“You’ll have to wait,” Dean said. He gave Cas a sideways kiss and spoke into the boy’s hair. “I want it to be a surprise.”

“Okay,” Cas smiled.

“But you absolutely do not have to say yes if it’s something you don’t want to do,” Dean’s tone was forceful and bold. It made Cas shiver as he nodded.

“O-okay,” His voice came out in a whisper, only a little bit breathless. Cas realized then that he liked when Dean used that voice; the dominant and commanding one.

“You okay?” Dean asked, leaning his head on Cas’s.

“Y-yeah,” Cas stuttered.

“Are you cold?”

Cas shook his head. “No... I just... I like the voice you just used.”

“Which one?” Dean asked. “My captain voice?”

“I guess so, I don’t know. The one you used to tell me I could say no to whatever you’re planning tomorrow,” Cas could feel himself blushing.

“That’s my captain voice,” Dean laughed. “You like it?” Cas nodded his head again. _“_ _Does it turn you on, Cas. ”_

Cas shivered again when he used the voice to make his question seem like more of a statement. “A little.”

“That is so good to know,” Dean laughed as he stroked Cas’s back gently for a while before speaking again. “Do you want to go to sleep?”

Cas nodded sleepily, “Yeah.”

“Okay, angel,” Dean murmured, helping Cas to get under the covers.

“Let’s sleep,” Cas mumbled as Dean pulled Cas’s back into his chest and kissed the nape of the boy’s neck until he fell asleep.

~  ~  ~

_February 22, 1693_

 

Cas woke up the next morning to the feel of Dean behind him and their hands laced together. He decided it was his favorite way to wake up and the perfect way to start this day.

Dean was snoring into the back of Cas’s head, not loud enough for it to be a nuisance. Cas found it cute. He liked knowing that Dean was able to get a good night’s sleep.

A moment later Dean sighed and stretched his legs. “Morning,” he said groggily. “What time is it?”

Cas looked up at the time keeper, “Eight o’clock-ish.”

“Perfect,” He said, moving his hand on to Cas’s stomach and slowly sliding it farther down.

“Dean,” Cas sighed, putting his palm on the man’s forearm as his hand disappeared into Cas’s trousers.

“Best way to wake up in the morning,” Dean laughed, taking hold of Cas’s cock and stroking it. Cas whimpered and thrust his hips slightly. “You want me to take your cock out of your pants?” Dean asked, his mouth right next to Cas’s ear. “Take you into my mouth and make you come?” Dean gave the boy enough time to whimper out a feeble _yes_  before he swiftly crawled on top of Cas and slotted himself between the boy's legs. “Happy birthday, my angel.” He pulled Cas’s cock out and gave him a few quick strokes, making him gasp in surprise. Dean smiled smugly and gave Cas a quick kiss before sliding down to be level with Cas's groin.

“Please,” Cas whispered, watching Dean closely as the man leaned down and wrapped his lips around the head of his cock, sucking the shaft down shortly after. Dean flattened his tongue and bobbed his head quickly as Cas gripped the sheets below him until his knuckles turned white and he was gasping for breath. He felt his release start to build quickly, residual sleepiness heightening his pleasure. But as soon as he was about to come, Dean pulled off and crawled up to kiss Cas.

Dean pushed his tongue into the blue-eyed boy’s mouth, silencing his cries of denial. Cas wrapped his legs around Dean’s waist in hopes of getting friction where he needed it most. Dean broke the kiss to stop his legs from encircling him and pushing them apart at the knees.

“Not so fast, angel,” He teased. Sliding down again and swallowing Cas back into his mouth, the boy gasped out a moan that sounded enough like it could be Dean's name. Dean tugged the clothes on Cas’s lower half off and chucked them behind him, never letting Cas slip out of his mouth.

The boy gripped Dean’s hair, mewling and bucking his hips into the man's mouth. “I’m so close!” Cas whined. Dean smirked and pulled off slowly with a final flick of his tongue across Cas's slit. Cas cried out, _“_ _No_ _!”_ And tried to push Dean’s mouth back onto his painfully hard cock. Dean sat up, moving back to connect his lips with Cas's as he blindly reached out for the oil. Cas gripped at Dean's hair and scratched at his scalp, whining unintelligible pleas into Dean's mouth while the man coated his fingers with the oil.

“Sh, baby," Dean soothed, pressing the pad of his finger against Cas's rim and rubbing against the sensitive ring. Cas inhaled sharply and his head fell back onto the pillows as a soft moan spilled out of his mouth. He breathed out a pleased sigh, thrusting his hips shallowly down in hopes of Dean's finger pushing into him.

"Dean," Cas whispered in a rough voice. He planted his feet and fucked his hips down in a calculated way that had Dean's digit inside him in a second. Cas yelped loudly at the burst of white hot pleasure that shot through him violently.

Dean put his hand on Cas's stomach to still his hips and slowly pumped his finger into Cas, curling them only slightly. "Did I hit your prostate?” Dean asked, licking his lips. Cas nodded and let out a broken whine. “Do you think you could come from just my fingers?” Cas arched his back and bucked himself down to meet Dean’s hand. “I’m gonna take that as a yes.” The pirate added another finger and made sure to bend them in just the right way. Cas started to let pitiful whimpers out and Dean realized then he was too good at his job.

The muscles in Cas’s abdomen tensed up and he knew the angel was close. Dean stopped and pulled his fingers out. Cas’s hips bucked wildly and he whimpered out a breathy and desolate _please!_ Dean leaned back down to kiss the whimpering boy, coaxing him back from the brink of orgasm.

“Please, Dean,” Cas asked, his eyes closed and tears leaking out of the corner.

“Use your words, angel,” Dean said, using his captain voice.

Cas trembled violently before he firmly nudged Dean onto his back and quickly pushed the man’s trousers down to his thighs. “Where’s the oil?” he asked, not able to focus on anything but trying to find it. Dean handed it to him and Cas got busy lathering the man’s cock up with more than enough oil. 

“Cas, go slow,” Dean said, putting his hands on the boy’s hips.“Be quiet, Dean!” Cas said breathlessly as he lined the head of Dean’s cock up with his entrance and immediately sunk down.

“Oh, my god,” Cas gasped for air. “Dean, oh, my god.” He bottomed out, smiling a little at the feeling of Dean's thighs beneath him.

“Fuck, Cas!” Dean almost shouted, Cas gasped and barely registered the feeling of Dean squeezing his hands through the deafening pleasure flowing through him with each beat of his heart. He whimpered and hung onto Dean with blinding strength until he was able to think clearly.

“Tell me what to do,” Cas said, grindings his hips into Dean.

“Put your hands behind your head,” Dean said, using his Captain voice again. Cas locked his fingers together behind his head and looked to Dean for more instruction. Dean raked his eyes up and down Cas’s body hungrily before issuing another command. “Fuck yourself on my cock." Cas whimpered and raised himself up an inch or so. Any more and he wouldn't be able to handle it. "Talk to me, tell me how it feels."

Cas cried out as he sank back down onto Dean's cock. He struggled to keep his hands behind his head. “You’re making me lose my mind! It’s so _intense!"_ Cas breathed out, closing his eyes. "Something about... Something about being on top of you makes it... So... _Intense._ "

“You want to come?” Dean asked, his hands getting dangerously close to the boy’s cock.

“Yes, Captain, please touch me,” Cas pleaded, looking down into Dean’s eyes. “Want you to make me come.”

Dean’s eyes flashed and the next thing he knew Dean had flipped them over and was pounding into the boy with no mercy. He was growling into Cas’s ear, “You want to come on my cock?”

Cas scrambled to find purchase anywhere on Dean’s chest or back. “Yes! Yes, yes Dean, please!” His mouth hung open and sobs were fucked out of him. “I’m so close.”

Dean slowed his hips to an agonizing pace for the boy, making him cry out and cling to Dean tightly. He bit down where the pirates neck met his shoulder and let out a muffled cry. “How bad do you want to come?” Dean asked, nipping at Cas’s ear lobe and jerking his hips forward, hitting his prostate dead on.

Cas threw his head back with his mouth open in a silent scream and arched his back into Dean violently, digging his nails into the man’s broad arms. He heard Dean cry out from somewhere far away. Cas was far too gone to be able to focus on anything but the feeling of Dean’s cock moving inside him.

Two more thrusts and Cas was coming; white ribbons of cum painted his chest.

 _“Cas!”_ The feeling of of the boy’s already _unbelievably_ tight heat clenching around Dean pulled him over the edge and he came inside Cas, thrusting shallowly through his orgasm. Dean kissed praises into the skin over Cas’s face and neck: _so good for me, beautiful, amazing, my angel, so perfect_ . Cas responded with pitched _thank you_ breaths and whimpered _yeah_ s.

They stayed like that for a long time before either of them moved. Cas felt something wet on the tips of his fingers. He looked at them and gasped in panic. “Exactly,” Dean pushed his face into Cas’s neck. “Breakfast should be ready by now.”

“We have to clean up before we go out,” Cas said, twirling locks of Dean’s hair between his fingers. Cas could practically feel Dean’s smirk before he saw it.

“Wanna help me shower?” He asked, a pleased smirk on his face.

~  ~  ~

Three hours and thirty minutes later, Dean and Cas were arriving at the lake. He’d spent the morning and some of the afternoon with Charlie, Gilda, Benny, Sam, Kevin, Ash, and Jo; opening presents and stuffing himself with amazing food. But now it was just Dean and Cas.

“Wow,” Cas breathed out, “It’s beautiful.”

“Like you,” Dean said, giving Cas his hand to help him down some rocks. Cas rolled his eyes, but smiled at Dean before looking back at the lake.

“There’s a waterfall?” he asked, jumping down next to Dean.

“Yeah,” Dean answered, smiling. “What do you want to do first?”

The two came to a stop near the water’s edge. “We should swim.”

Dean smiled and dropped everything to the ground. “Let’s do it,” he said and began undressing. Back on the boat they had both decided they wouldn’t need any swim clothes. Cas blushed, only a little, and did the same. He took Dean's hand in his when they were both undressed and let Dean lead him to the waters edge. Slowly edging himself in, Cas found it to be the perfect temperature.

“There’s a geyser or something way down at the bottom, it keeps the water warm year-round,” Dean told him, smiling when Cas finally made it waist deep.

“How do you know?”

“Sam helped me find this place and test the water. He’s a huge science-enthusiast,” Dean waded over to Cas, “Water fight?” Cas giggled and attacked first, shoving water into Dean’s face and swimming away. He heard Dean’s laugh and then splashing water as the pirate swam toward him. Cas realized he was _going_ to get caught; Dean spent his life on the water.

“Gotcha!” Dean yelled, wrapping an arm around Cas’s waist. The younger boy squealed and kicked his legs, making Dean fall backwards underwater and let go of Cas’s waist. He was able to get away from Dean and swam back towards the bank.

Cas risked a look behind him but couldn’t see Dean. He stopped and treaded water, looking for any sign of his lover. There was no sign of him, though.

“Dean?” Cas called out, getting slightly worried. He didn’t register the sound of water moving behind him until it was too late and Dean was wrapping his arms around Cas and pulling him back towards the bank. Cas yelped in surprise before laughing as he let Dean drag him up to a spot where he could be laid down, halfway in the water.

The taller man was above him in seconds and beaming at Cas. “I win,” He said, and leaned down to kiss the smaller boy.

Cas snaked his arms around Dean’s neck and smiled against his lips. “You did.” They both laughed and kissed some more before getting back into the water and swimming together.

When they were done swimming it was already three in the afternoon.

“What do you feel like doing now?” Dean asked, grabbing a towel for the smaller boy.

“Cuddle.”

Dean laughed, “Sounds good to me,” he said and pulled out the picnic blanket he brought. Cas helped him to smooth the wrinkles out before they both laid down next to each other. Dean’s arms around Cas and their legs slotted together in a pattern of _Cas-Dean-Cas-Dean_. They laid like that together, relaxing after their swim, for a long while.

“Dean, may I ask you a question?” Cas asked, looking up at Dean.

“Of course. You know you can ask me anything.”

“Why did you say yes to seeing me again? After our first night together.”

“Well, Cas, I don’t really know,” Dean admitted. “I thought about this a lot when I was out at sea, and I couldn’t think of an answer. There was just something about you that made me feel like I had to see you again and I needed to protect you…”

“You barely even knew me,” Cas stated.

“Aye,” Dean nodded, “But there was something that told me that you were special. I mean, _I_ know you’re special. But there was something else that was telling me you were. And you are.”

“What do you mean?”

“I don’t know,” Dean pressed his forehead against Cas’s. “It’s as if, there was me telling myself that you were special and I wanted to get to know you. But there was another thing or being, or whatever, whispering in my ear and confirming you were — _are_ — special. And that it was my duty to protect you.”

Cas smiled as he spoke. “From what?”

“Anything and everything,” Dean responded. “What about you? What made you want to see me again?”

“I was scared,” Cas admitted. “My father’s been abusing me ever since I can remember, and being near you made me feel… Well, _protected_.”

“You should’ve told me about your father sooner,” Dean scolded.

“What could you have done?” Cas asked, taking a deep breath. “It’s just something I have to deal with.”

Dean pulled Cas in closer to his body, “I don’t like seeing you hurt.”

“I know,” Cas whispered. “But I’ll be okay.”

“What if you’re not? What if one day Michael takes it too far and what if-”

“Dean,” Cas interjected, “Those are _what if_ ’s.”

“I care about you,” Dean whispered, closing his eyes and breathing deeply. “I want to protect you.”

“You are — You _do_ protect me.”

Dean rolled on top of Cas, pinning his arms above his head and forcing Cas’s legs to fall open and frame the pirates hips. “I can’t protect you when I’m not here, though. And I can’t take you with me. If anything happened to you… I could never be able to forgive myself.”

Cas wrapped his legs around Dean’s hips, digging his heels into the back of Dean’s thighs to pull him closer. “I don’t blame you for having to go to sea, Dean,” he whispered, green eyes searched blue and vice versa. “You’re not leaving me.”

“I’d never leave _you_ , Cas.” Dean’s eyes darted between Cas’s.

“I know.” Cas made a show of licking his lips; Dean’s eyes flicked down to them to watch. “Dean, kiss me?”

The pirate’s lips were on his in a second and his hands went from pinning Cas’s wrists down to holding his hands. Cas opened his mouth and let Dean’s tongue plunge in to tangle together with Cas’s.

~  ~  ~

Dean and Cas were met with a chorus of _hey_ ’s from the regular group, plus a few other’s Cas didn’t know, as they boarded the ship again. It was about nine o’clock and the sun had set two hours ago. It got very cold very fast by the lake, and Dean could only produce so much heat to keep himself as well as Cas’s small body warm.

“How was it?” Gilda said.

“It was really fun,” Cas nodded, leaning into Dean’s body for support.

Dean looked down at him and smiled warmly. “It was. But we we’re a little tired. So we’re just going to head in.”

“Of course,” Jo said, hiding her smirk into her glass. “You’re going to _sleep_ together.”

Dean rolled his eyes, “Ha, ha, ha, Jo,” He said, smiling still. “That’s so funny.”

“Get out of here,” Charlie stood up with an empty pitcher of what used to be Benny’s grog.

“Thanks Charlie,” Dean said.

“I’ll see you all later,” Cas called over his shoulder, earning a cheer from the group. Dean and Cas made their way to Dean’s cabin again, kissing when no one was looking.

As they got into the room, Dean picked Cas up and pushed him against the door, making him gasp in surprise. The pirate moved to nip at Cas’s neck while on of his hands came to palm at Cas’s groin while the other supported some of his weight under his thigh.  

“Dean,” Cas gasped again and squeezed his legs around Dean’s waist. “W-What did y-you want to try with m-me?”

Dean laughed against Cas’s neck before sliding his hand from Cas’s groin to his other thigh and carrying them to the bed. He dropped Cas down and let him giggle as he bounced a little before spreading himself out on the sheets; a moment later Dean was between Cas’s legs and his lips were on the boy’s neck.

“Dean,” Cas moaned, sliding his hip against Dean’s and feeling the quickly growing bulge in the pirates pants. He let out a small whimper before pulling at Dean’s shirt. “I want you undressed. Now,” Cas whined. “Pants.” Dean laughed and let Cas undo his trousers, immediately shoving his hand into them and wrapping his hand around Dean’s shaft. He opened Dean’s pants enough to get his cock out without actually taking his pants off. Cas was too engrossed with stroking Dean’s cock at the moment to worry about the rest of his clothes.

“That feels good,” Dean moaned, kissing Cas’s neck.

“Yeah?” Cas asked breathlessly. Dean groaned in response. “I like when I can make you feel good.” Dean laughed into Cas’s neck and ended it with a kiss. Cas slowed his hand, making Dean raise his head to look at Cas. The smaller man smiled and swiped his thumb over the slit of Dean’s cock, collecting the precome that started to seep out. He brought it up to his mouth and licked it off.

Dean watched his mouth intently before tensing. “ _Oh_ ,” he moaned, jerking back and stopping the hand Cas still had on his shaft.

The younger boy licked his lips and smiled triumphantly, “Were you about to come?”

Dean breathed hard, sitting back on his knees. “I’m only giving you this one, since it’s your birthday.”

“So that’s a yes?”

“Yes, I was. But I have more planned and I can’t have you ruining it by making me come so embarrassingly early.” Dean leaned back over Cas, hovering over his lips as he reached into his nightstand and grabbed the oil, as well as something else. He leaned back and held his hand behind his back.

Cas eyes him suspiciously, “What have you go behind your back?”

Dean smiled, “This is part of what I wanted to try with you.”

“What is it?”

“Well,” Dean pulled his hand back out.

Cas asked, his eyes widening and his heart racing in excitement. “Rope?” 

“I want to tie your hands up,” Dean stated. “You squarely do not have to say yes to this.” He set the rope down and rubbed Cas’s thighs. “I wanted to have this all about you. I want to give you a good birthday.”

Cas felt his breath catch and his cock twitch. “Yes.”

“Seriously?” Dean stared at him. “Don’t feel like you have to say yes, Cas. If you don’t want to, I won’t be disappointed or upset.”

Cas desperately clawed at his clothes. “Yes, Dean. Help me get these off.” Dean smiled and laughed, leaning down and kissing the boy beneath him. His hands came to push Cas’s shirt up to pool under his arms. Cas whined into Dean’s mouth and pulled his shirt off the rest of the way.

“Eager, are we?” Dean teased. Cas bit down on Dean’s lip; not hard enough to hurt, but hard enough to make the pirate shut up. Dean chuckled and continued to kiss the boy beneath him as he slid Cas’s pants and drawers off.

 _“Your clothes, too.”_ clothes, too.”

“As you wish, angel,” Dean whispered, making quick work of shedding his shirts and trousers.

“Take your drawers off, as well, Dean.” Cas glared at the pirate. _Dean.”_ Cas glared at the pirate.

“Impatient,” Dean hissed playfully, smiling afterwards and taking his under-linens off. Cas basked in the view of Dean’s form as the man took Cas’s wrists in his hands and pushed them up towards the head bed. “Don’t move them.”

“Yes, Captain.” Cas said breathlessly.

Dean grabbed the rope and threaded it through the slats of his headboard, pausing before wrapping the rope around Cas’s wrists. “We need a safeword?”

“What do you mean?” Cas asked, his voice coming out whinier than he wanted.

“If it gets to be too much for you we need something for you to say to let me know to stop.”

“What about stop?” Cas asked, furrowing his brows at Dean. _"Stop?”_ Cas asked, furrowing his brows at Dean.

“Well, I mean,” Dean shrugged. “That could work, yes, but I was thinking something more along the lines of a word you wouldn’t say during sex.”

“I like peaches,” Cas said, trying to ignore his aching cock. “So, peach?”

“Perfect,” Dean smiled. “Plus, that way… You can say stop or no or whatever and I know I don’t actually have to stop. It sounds odd, but trust me, I think you’ll like the feeling of being—”

“Helpless,” Cas breathed out, feeling blood rush to his groin. “I see why you’d use something other than stop.”

“Seemingly helpless,” Dean laughed before taking Cas’s hands again and tying the rope around them securely. “How does that feel? Is it too tight?”

Cas tested the restraints and shook his head. “No, it’s perfect.”

Dean nodded, “I’ll check in with you with colors, okay? Green means to keep going, yellow means to pause for a second, and red means to stop.”

“Okay,” Cas nodded, pulling on the rope around his wrists a little. “I’ll remember.”

Dean kissed Cas quickly before sitting up and smiling at his angel; he didn’t do anything for a while as his eyes went from Cas’s face to his torso, down his legs and back to his face again. “You’re so beautiful.”

“God, Dean,” Cas groaned. “We only have so many hours left of my birthday.”

“Patience, patience,” Dean used his captain voice, making Cas whine. The pirate splayed his hands on the boy’s stomach and slowly ran them up his body, savoring the feel of the angel’s skin under his hands. “I’m serious, Cas; you’re _stunnin g_ _.” Cas was at a loss for words. Something about the way Dean was looking at him made Cas want to cry from happiness._ Cas was at a loss for words. Something about the way Dean was looking at him made him want to cry from happiness.

“Dean… Thank you,” Cas stuttered out, smiling. Dean leaned down and kissed Cas lovingly, moving his lips slow and steady against Cas’s until they were breathing hard. He moved his hands up to play with Cas’s nipples until the boy was squirming beneath him and whimpering against Dean’s mouth.

“Please,” Cas whined, bucking his hips into Dean’s. The taller man nodded, oiling his fingers up and pressing them into Cas slowly, making the boy moan and writhe even more.

“Talk to me,” Dean commanded.

 _“Ah!_ Dean you always make me feel so good,” Cas gasped and strained against his bonds. Dean smiled to himself. He crooked his fingers and watched as Cas sharply inhale a shaky breath and shiver. “Oh my god, right there, please. Right _there_.”

“Yeah?”

“Yes,” Cas whimpered and opened his legs wider. "Don't stop. Please don't stop!"

"I won't," Dean said lowly, watching Cas's face closely. He always made the prettiest faces. And the fact that Dean was the one who caused him to make such faces only made Dean feel like he was special. Not only that, but he was the only one who had ever seen Cas at this state and he was the only one Cas would let see him like this.

“Dean! Oh, my _god!_ You’re gonna make me come!” Cas whined, pulling Dean out of his thoughts.

“Don’t,” Dean said in the dominant voice that made Cas shiver with need.

“Please!” Cas pulled on the ropes around his wrists. “Dean, oh my god, please?”

“Don’t come,” Dean said again, adding another finger and making the boy just about scream as he rubbed against Cas's prostate relentlessly.

“Dean,” Cas mewled, looking at Dean with hazy eyes. “Please… Please… Please…”

“Please what?” Dean whispered. Cas squeezed his legs around Dean. "Please let you come?" Cas nodded frantically, his legs starting to shake from how hard he was squeezing them around Dean's hips. The pirate smirked and pulled his fingers out. “Color?”

“Dean!” Cas howled in frustration, jerking his hips back down towards Dean's hand. “Green.”

Dean hummed, “You’re not really used to _this._ ” He massaged the inner parts of Cas’s thighs with his thumbs. “You’ve been spoiled, haven’t you?”

“Yes,” Cas whined, spreading his legs wider for Dean.

“Yes, _what?”_

“Yes _Captain,_ ” Cas honestly cried.

“Good,” Dean purred. He let his hands come dangerously close to Cas’s cock before moving them past and stroking the boy’s sides. “Color?”

Cas didn’t hesitate in answering, “Green.” Dean nodded, the corners of his mouth twitching up. He kept moving his hands up Cas’s body and down; just close enough to make Cas squirm.

“What do you want me to do to you, Cas?” Dean whispered, giving Cas a smug look. Cas didn't answer and instead kept his attention on Dean's hands. Dean doubted Cas had even registered any words were spoken. "Cas." Dean said firmly, taking his hands off of the boy.

"No, please," he whined as his cock twiched against his abdomen and a generous amount of precome dribbled out.

"What do you want me to do?" Dean repeated. Cas threw his head back in frustration, letting out a high pitched groan. "Do you want me to suck you off? Fuck my fingers into while I’m at it?" Cas snapped his head back up to look at Dean, his eyes looking close to tears. "Or do you want me to fuck you, good and hard? Take your cock in my hand and jerk you off as I pound into you?” Cas let out an involuntary strangled cry as Dean put his hands back on him and he brushed a thumb past the base of the boy's cock. “What do you want, Cas?”

“I want you to _fuck me_ , Dean!” Cas begged, thrusting his hips up again. Dean had to take a moment to comprise himself. Cas had just cursed in front of him. Cas - the walking definition of innocence - had _swore_ in front of him.

“Cas,” Dean tsked him. “Where did your manners go?”

“Please,” Cas whined desperately, his hips making small thrusting movements. Dean looked down at the boy’s cock: swollen, red at the tip, and leaking precome. “Please?”

Dean shushed the boy by pushing an oiled finger into his hole. Cas moaned and threw his head back; he gasped out frenzied words that turned into only sounds seconds later. Dean added two more fingers in rapid succession, watching as Cas’s eyes screwed themselves shut and his hips jerked down to meet Dean’s fingers.

“You like being tied up, don’t you,” Dean spoke in a deep voice. Cas’s legs jerked open wider. “You like being helpless to me.”

Cas nodded his head wildly and bit his lip as he hummed, “Mh-hm.”

Dean moved his fingers in a ‘come hither’ motion and arched and eyebrow as Cas’s body convulsed and he came, his mouth falling open in a silent scream. He didn’t stop until Cas was panting and clenching his legs around Dean in an attempt to get the older man to stop.

“Please…” Cas heaved, pulling on his restraints helplessly. Dean pulled his fingers out and looked at the line of white coating Cas’s chest. He shook his head and clicked his tongue.

“You disobeyed,” Dean stated, palming Cas’s cock gently. Cas jerked away from Dean’s hand violently, yelping at the same time. “Color?” Dean asked, taking his hand away.

“Green,” Cas responded, digging his heels into the bed to ground himself.

“Bloody fantastic,” Dean whispered, pushing Cas’s hips down into the bed and watched the boy’s face as he moved his hand back against his length..

“No,” Cas whimpered. “Dean, please!”

“Color?” Dean asked again, unsure if he should really continue.

Cas whimpered in annoyance and kicked at Dean’s legs enough to get his point across. _“_ _Green_ _!”_ Dean felt himself smile.

“Well, Cas,” Dean said as he took Cas’s shaft in his hand and pumped his fist. “You disobeyed an order.”

Cas looked straight into Dean’s eyes. “Stop,” he whispered hoarsely. Dean felt like he was just punched in the stomach. Cas’s eyes were wide and pleading for Dean _not_ to stop. “Stop!”

“You need to learn your lesson,” Dean drawled out.

Cas gasped and pulled harder at his bonds. “I have! I have! Please stop, I have!”

Dean felt Cas start to get hard again and his shaky legs clench around his waist. He quickened his hands, making Cas stutter out a cry. “Will you be coming without permission?”

Cas sobbed, “No! I promise!” The pirate let go of Cas's semi hard cock and massaged his sides.

“Color?”

“Green.”

“How are you doing?” Dean asked, cupping Cas’s face with one hand while the other continued to rub at Cas’s side. “Was that too much?”

Cas shook his head, “No,” he whispered, closing his eyes. “No, it wasn’t. I feel very good.”

Dean smiled, leaning down to kiss away Cas's tears. He trailed his lips down to brush against the boy's a whispered, “You did such a good job, baby." Dean kissed Cas slowly. "I'm so proud of you." 

“Thank you,” Cas huffed out, letting his legs fall open again.  

 

Dean chuckled as he waited for Cas to recover. “Tell me when you want to go on.” 

“Just give me a second,” Cas spoke, turning his head to let Dean kiss down his cheek and jaw.

“Of course,” Dean murmured, kissing his way to Cas’s neck. Cas sighed and moved his body into Dean, biting his lip in a pleased manner at the warmth Dean gave off. “You’re so perfect,” Dean mumbled into Cas’s skin, dragging his lips over every possible inch of Cas’s neck as he could.

“Okay,” Cas moaned and arched into Dean’s touches. “I want you to keep going.”

“Are you sure?”

“Yes,” Cas said, bucking his hips into Dean’s. Dean got the message and sat up on his heels. He took his member in his hand and caught Cas’s eyes as he lowered his hips to Cas’s to grip the smaller boy’s cock in the same hand.

Cas gasped and his eyes rolled up into his head. “Do you feel that?” Dean asked, thrusting his hips and rubbing their shafts together.

Cas whimpered out, “F-feel what?”

"Me," Dean whispered, burying his face in Cas's neck. "Me against you." 

"Y-yeah," Cas breathed out. 

"Good," Dean almost growled; a hint of possessiveness in his voice. "You feel how hard you get me?"

"Yes, Dean," Cas whispered, his jaw falling open as he felt heat pool in the pit of his stomach again.

“You do?”

“Yes,” Cas cried, thrusting his own hips in Dean’s hand and heaving again at the sensation of the older man’s length against his own.

“You like having our cocks against each other?”

“Yes,” he gasped, letting out a pitiful whine as Dean let go and it was just their shafts moving against each other. Dean pinned down Cas’s hips and pushed his own forward and back teasingly. Cas threw his head back and inhaled deeply.

“You want to come again?” Dean asked, leaning down to speak in Cas’s ear.

“Mh-hm,” Cas whimpered.

“You like the feel of my cock against yours that much?” Dean said in a husky voice.

Cas shivered with need and bit his lip. “Please,” he whined, trying to thrust his hips.

“I’m going too slow to get you there, aren’t I?”

Cas hiccuped out a sob. “Yeah.”

“It’s so frustrating, isn’t it?”

“Yes!” Cas wailed. He turned his head into Dean’s to kiss him. But, Dean pulled away. He didn’t give any sort of satisfaction to the boy beneath him.

“Color?”

“Green.”

“What do you want me to do?” Dean asked, giving a sharp thrust of his hips and making Cas curl in towards Dean in surprise.

“Please,” Cas whined, making eye contact with his lover. “Please.”

“Use your words,” Dean demanded.

“Please fuck me,” Cas whispered, blushing slightly at the dirty word. “Please, I want to feel your cock inside me.”

“Is that so?” Dean teased, smirking. He gave another violent thrust of his hips against Cas.

“Yes!” Cas screamed, panting hard. “Please I’m begging!”

“Say the magic words,” Dean ordered, very slowly pushing his hips forward. Cas’s eyes lolled back into his head as he let out a long, low moan. Dean smiled at the mess Cas was becoming. “Say it.” Dean stopped his hips and pulled away from Cas. He took his length in his hand and stroked himself. Cas panted for a few minutes before opening his eyes and fixing his gaze on Dean’s hands. He let out a string of desperate whimpers and moans. The boy was so far past being able to speak, it only made the pirate harder. Dean grunted the boy’s name. “ _Say it._ ”

Cas gasped and opened his mouth, moaning out Dean’s name. He breathed hard while watching Dean’s hand. “Please… Captain…” Cas’s eyes shot up to Dean’s and begged him for release.

Dean groaned and stopped his hand. He grabbed the oil and quickly oiled his cock up before lining his head up with Cas’s entrance. “You can come,” Dean started, “But if you come, I’m not stopping until I’m finished.” Cas pouted while he tried to push himself down onto Dean’s thick length. He wanted more than anything to be filled up by the pirate. “Do you understand?” Cas nodded eagerly, whining loudly. “Nod your head if your color is green.”

Cas nodded his head again, letting out an almost pained whine, and Dean smirked, pushing in slowly and drawing out a loud, pitched moan from Cas. Dean moved his hands down to Cas’s ankles as he bottomed out and held them apart and started thrusting his hips slowly. Cas was barely given any time to rest his voice from the elongated moans spilling from his mouth. “You want me to go faster?” Dean asked, his voice breathless. Cas bobbed his head up and down. “You want me to fuck you harder?”

Cas let out a loud, breathy moan. “Please…” he begged, sounding only sounded like he’d breathed out the _p_ and _s_ sound. Dean smiled and fucked into Cas with reverence, angling his hips up to hit the boy’s prostate.

Cas screamed out Dean’s name each time he thrust in. At some point, the name just became a jumble of vowels.

“You wanna come,” Dean stated. “Then come.”

Cas pulled at the rope around his wrists and went silent for a second before he spasmed forward violently. Dean watched the boy’s face as he came a second later with a violent thrust of Dean’s hips into his prostate. The look of _pure_ bliss that washed over Cas’s features was too much for the pirate to handle and Dean threw his head back as he came, collapsing on top of Cas afterward. He breathed hard as Cas wrapped his legs around Dean and they both rode the aftershocks of their orgasms out. Cas squeezed his legs around Dean every now and then as he felt another shot of pleasure run through him. 

“Cas,” He groaned as he pushed himself up to untie the boy’s hands. “How are you feeling?”

“I want to do that again,” Cas mumbled, bringing his arms into his chest. “I want you to completely tie me up.”

“Your legs, too?”

“Yes,” Cas sighed, letting Dean unwrap his legs from the man's waist so he could clean them both up.

“You, uh…” Dean flopped down next to Cas after he wiped off the cum from the boy’s chest. “Are you sure I didn’t go too far?”

Cas snuggled up next to the larger man. “No, I—” he stopped to yawn. “I liked it. But my wrists are rather sore.”

“So not an every time thing, then,” Dean suggested, pulling Cas closer into his body.

“Just for special occasions,” Cas agreed, ending his sentence with a big, content sigh.

“Sounds good to me, baby,” Dean kissed his angel’s forehead. “You go to sleep, now. I’ll wake us up tomorrow.”

“Thank you, Dean,” Cas mumbled, kissing Dean’s collarbone.

Dean smiled, closing his eyes and holding Cas close to his body. “Happy birthday, my angel.”

**Notes for the Chapter:**

> I am so sorry for how long it took me to update! I've been rather busy with the things going on in my life. I just turned 18 and for some reason, my mom has now decided to go absolutely crazy so not only do I have to deal with that until I move out (which I'm working on at the moment and is one of the reasons for the late update) but I also have to deal with the extra chores (that used to be her chores) she gives me as well as studying to take my GED so I can actually finally get accepted for a job so I /can/ move out and just agh I'm sorry. It doesn't matter. I'm hoping the next chapter won't take as long to get up. 
> 
> Thank you all for your support and love for this story!


	7. Chapter Seven

Chapter Seven

_March 3, 1693_

It started storming three days before Dean had to leave again, and it hadn't let up since. Cas had been worried about the crew going out on the water in the weather. He’d heard of horror stories of ships capsizing and whole crew’s dying. He didn’t want that to happen to anyone on the Impala.

Cas begged Dean to stay until the weather calmed down, but Dean had said he couldn’t.

“Please?” Cas asked, gripping onto Dean’s hands while they made love. “Please stay; just one more week.” Cas ended his words with a gasp as Dean thrust into him.

“I can’t,” Dean whispered, thrusting his hips harder into Cas and making the boy whimper.

“I can’t — ah! — lose you,” Cas cried. Dean quickened his hips and looked into Cas’s eyes.

“Come,” he commanded, watching in awe when a moment later Cas’s mouth fell open and his back arched into Dean’s chest. A high pitched moan tore itself out of his throat and Cas came. Dean followed him soon after placing sloppy kisses over Cas’s face until they were able to talk.

“Please,” Cas cried again. “What if you don’t come back?”

“That’s a what if,” Dean said, pulling out of Cas and burying his face in his lover’s neck. “I’ll _always_ come back to you.”

“It’s been storming for three days,” Cas stated, wrapping his arms around Dean’s shoulders. “The sea is going to be dangerous.”

“Aye,” Dean nodded and kissed Cas’s neck, “But I’m coming back, Cas. Nothing can stop me from coming back to be by your side.”

“You can’t promise that, Dean.” Cas turned his head away, feeling more tears spill out of his eyes. “You don’t know what the future holds.”

“Nay,” Dean said, “I do. I’m _going_ to come back and I’m going to _keep_ coming back to you; for as long as you’ll have me.”

Cas laced his fingers into Dean’s hair. “Forever.” He held the pirate close to him and clung onto his body. “I want you for the rest of my life.”

Dean’s voice came out shaky, “Cas…” He was crying. He grabbed the boy’s chin and made their eyes meet. There were no more words Dean could say at this moment to make Cas understand what he was feeling. Desperate lips and hands explored the boy’s body, as if he were memorizing every single curve Cas had to offer.

“I don’t want to lose you,” Cas hiccupped out a sob. He pulled Dean’s head up from his neck to his to connect their lips in a chaste kiss before speaking, “You _have_ to come back to me.”

Dean nodded his head, smiling a little and put his forehead against Cas’s. “Always.”

Cas's voice cracked and filled with tears as he said, “You’re _mine_ ... My beautiful… _Beautiful_ pirate.” Cas sucked in a shaky breath, closing his eyes and tightening his legs around Dean’s waist.

“I’m yours,” Dean echoed. “I’m _yours_.”

Cas opened his eyes to look into Dean’s. He felt his chest expand with emotion for the devastatingly stunning man. “Fuck me?" Cas pleaded, "Fuck me again.”

Dean breathed in through his nose, “No.”

“Please,” Cas begged. “Please, Dean.”

The pirate shook his head. “No.” He kissed Cas tenderly, “I won’t fuck you.” He reached his hand down between them and took Cas’s length in his palm, stroking him lovingly. “We aren’t going to _fuck_.”

“Then make love to me,” He gasped, clinging to Dean as he felt the man’s half-hard cock push into him again slowly. Cas whined Dean’s name, not entirely sure what he was wanting.

“Sh,” Dean whispered, his hands coming to hold Cas as close as he could. “I got you, baby. I’m never letting you go.”

“Dean!” Cas whimpered, holding onto Dean with all of his strength as Dean thrust into him, slow and deep. It made Cas ache. It made him ache so _beautifully_ to be touched that deep. It drove him absolutely crazy. His fingers dug bruises into Dean’s arms and back while his nails left angry red lines.

“I got you,” Dean whispered, “I got you, angel.” He pushed his face into Cas’s neck, breathing hard. Dean was still sensitive from earlier, making each thrust into Cas’s heat hurt in the most delicious way possible.

Cas bit down on Dean’s shoulder, muffling his sobs. He wanted to come so bad, but he didn’t want this to ever end; because when it ended, it meant Dean had to leave again and he was back to falling asleep in his own bed every night and feeling empty...

Cas gasped, writhing helplessly against Dean, “I love you!” He tightened his grip on Dean wherever he could. “I love you, Dean.”

The pirate kissed Cas’s neck, soft and tender, before responding. “I love you, too, Cas. I love you so much.” He was breathless and his thrusts getting faster and more agonizing.

“I love you!” Cas cried, saying the words each time Dean thrust into him. The pirate responding with desperate kisses against the boy’s neck and whispered _me too, Cas_ ’s.

Not even a minute later, Cas’s words turned into urgent gasps and whines. Dean lifted his head from Cas’s neck and looked into the boy’s eyes. They came at the same time, crushing their lips together and whispering _I love you_ ’s to each other and refusing to let go of one another.

Cas and Dean were content. They’d be happy to die like this if that’s what it came to: sloppy kisses and thrusts of hips; wonton _I love you_ ’s whispered against the other’s mouth, skin pressed against skin, and tears mixing together on their cheeks.

~  ~  ~

_March 4, 1693_

They woke up early the next morning with heavy hearts and sad eyes. Dean had to leave. And he wouldn’t be back for months. It wasn't different from the previous times that Dean left. But somehow it was also very different. That fact was as agonizing to Dean as it was to Cas. Dean wanted to stay or take his angel with him, but he couldn’t. Neither actions were options.

Not yet, at least.

“You have the necklace I gave you?” Dean asked, holding Cas against his body securely. Cas breathed in the man’s scent, trying to memorize it for the months to come.

“I do,” Cas nodded. Dean’s arms squeezed Cas tighter, making it almost hard to breathe for Cas. But he honestly didn’t even want to entertain the idea of minding the lack of oxygen.

“I promise,” Dean whispered, “I’ll be back soon.”

“Soon,” Cas agreed.

“I love you, Cas,” Dean was almost crying. “I love you so much.”

A few tears slipped out of Cas’s eyes and he hid them by burying his face into Dean’s chest. “I love you, too. Dean, I _really_ love you.” Cas felt Dean suck in a big, shaky breath. He was trying his hardest not to cry. If he started crying, he would never be able to leave. Dean had contracts to deal out and collect on. He couldn’t disregard his responsibilities.

They held each other for a minute more before Cas pushed the pirate away. “Go.” Dean searched his eyes as he took one small step backwards. Cas looked away. “Go, Dean. The sooner you go the sooner you come back.”

Dean choked on a laugh. “You’re right.”

“Go,” Cas smiled, looking back at Dean and playing with the gem around his neck.

“Okay.” Dean took more confident steps backwards, his eyes never leaving Cas’s before he had to turn around and make his way up the dock stairs to his ship.

Just like last time, Cas watched the ship leave until long after he couldn’t see it anymore. Part of him was staying because he hoped that Dean would turn the ship around and come right back and take him on the ship and never return to Heaven. He knew that wasn’t going to happen. Not yet.

 

_“Please, take me with you. There’s nothing here that I care about enough to stay for.”_

_“What about Gabe?”_

_“He can come with, too.”_

_“Cas…” Dean sighed._

_“_ Dean _.” Cas glared at the man._

_“Not yet.” The pirate said. “Not when you’re still so young.”_

_“You promise? When the time is right you’ll take with with you.”_

_Dean searched the boy’s eyes. “I promise.”_

 

When the time was right, Dean would make good on his promise and take him on board to become part of the pirates crew. But for now, they just had to deal with the separation that came with loving one another.

~  ~  ~

_June 13, 1693_

Three months out at sea had gone by. Three months without Cas… Torture.

Dean was in his cabin at his desk, trying to work out the logistics of how he’d be able to carry out this new deal some poor lovesick fool asked for.

“Hey,” Jo said, startling Dean slightly.

“Hey,” Dean responded, giving her a quick smile before looking back down at the document. “Is there something I can help you with?”

“You love him,” she stated. Dean froze before sighing and pushing his chair out to walk to his bed. Jo followed him, leaning up against the post at the foot of his bed.

“Yes.”

“Does he love you?”

“He thinks he does.”

“What do you mean by that?” Jo asked, pushing herself off the wall.

“Cas… He… He doesn’t love me. He's still so young and he's only ever been in Heaven. He doesn't know what love even is. All he knows is that I can show him a sort of pleasure he's never experienced before.”

“Fuck, Dean,” Jo exclaimed, exasperated. “You’re letting your past affect you! Anyone with eyes can see you two are bloody soulmates. Cas is head-over-fucking-heels in love with you.”

Dean felt like he had been shot in the chest from Jo’s comment about his past. _But_ she _was_ right. And Dean was decent enough to admit when he was wrong. “You’re right. I am letting my past get in the way of my present and future. But...” He replayed what Jo had said about Cas being head-over-heels for him and felt like he was going to die from sheer happiness; a smile tugged at his lips that he couldn’t help. “Is it that obvious?” Dean asked.

Jo laughed, “Cas in love with you? _Yes._ You in love with Cas…?” Her head tilted to the side in thought and she looked over Dean. “Not to everyone. Charlie and Gilda, Benny, and I know. Sam’s got an idea, but he’s also skeptical of Cas.”

“Why? What has Cas done to him?” Dean asked, furrowing his brows.

“Absolutely nothing,” Jo sighed. “He just doesn’t want you to get hurt.”

“That’s sweet of him, but I don’t need him to—”

Jo cut Dean off with a snort, “Doesn’t matter if you need him to or not, he’s your brother. But he’ll come to his senses. Just as Benny and I did.”

“Aye,” Dean nodded. He looked at Jo as she came to sit down next to him.

“You’ve been mopey for the past two months since we left. You used to joke a lot more than you do now, you know.” Dean felt like she was accusing him of something. “You’re not your regular self. And if I say so myself, it’s a little annoying.” He immediately went on the defense.

“I just miss Cas, Jo. Aren’t I allowed to grieve for a time before I go back to the way I used to be?” Dean said, immediately regretting the tone he used. Jo wasn’t trying to be mean. He knew she was trying to get a point across: _why don’t we take him with us?_ “I’m sorry.”

“Nay, it’s okay,” Jo said, “I understand.”

“Thank you,” Dean whispered, laying back on his bed and covering his eyes with a hand. “I know you want to ask me the question; go ahead.”

“Why don’t you take him along the next time we leave?” Jo asked, not beating around the bush. She knew that Dean wasn’t going to offer up that information.

Dean moved his hand to look at her, “You know why.”

Jo shook her head, “No. I don’t.”

“Life as a pirate,” Dean started, “It’s dangerous. I would never forgive myself if anything happened to him.”

“That’s bullshit and you know it.”

“What?” Dean pushed himself up into a sitting position again. “No it’s not.”

“Of all the years on your ship, do you know how many people from our crew I’ve seen die?” Jo asked, looking at Dean’s face with a hard expression.

Dean scoffed bitterly, “Too many.”

“Three,” Jo said. “Three crew members.”

“You’ve only been on my ship for four years, Jo.”

“Benny and Sam have been by your side since you bought your ship,” Jo pushed Dean to look at her. “Do you know how many crew members they’ve seen die?” Dean looked at her with a pained expression. “Three, Dean. _Three_.”

Dean closed his eyes, remembering what had happened that day. “It all happened so fast,” he said, opening his eyes to look at the ground. “The other ship was so fast at reloading their cannons.”

“It wasn’t your fault,” Jo said, taking Dean’s face between her hands and roughly forcing him to look at her. “Those three knew what they were getting into when they came aboard.”

Dean pushed Jo’s hands away and stood up. “I should have been ready, though, Jo. I’m Dean fucking Winchester of the Impala 67. I’m _The_ goddamn _Righteous Man_!”

“You’re also human, Dean,” Jo scolded. “You make mistakes.”

“Someone shouldn’t have to pay for my mistakes,” Dean shot Jo a look.

“Stop being childish.” Jo stood up, walking over to Dean. Even though she was about a head shorter than Dean, she was still scary as hell. “You _cannot_ blame yourself for everything! When that ship attacked us, _no one_ was ready. It wasn’t just you —  they came out of nowhere _and_ at night. You can’t hold yourself to a higher standard than everyone else. Not in a situation like this. You’re just one man.” Jo jabbed Dean’s chest.

“But—”

“No, Dean. No,” Jo said, “You just _can’t_. Do you understand?”

Dean nodded. “I do.”

“You’re human. And you make mistakes,” Jo said softly. She hugged Dean tightly. “But, those mistakes are not _who you are.”_

“I’m trying, Jo,” Dean said, wrapping his arms around Jo and resting his chin on her head.

“I know you are. I can see you’re trying very hard. But you just need to be reminded sometimes.” Jo gave Dean a squeeze before letting go and making a move to head out to the main deck. Before she could get to the door it flew open and a small boy ran in, crying. He bolted over to Dean and clung to the pirate’s leg.

“Whoa there, Ben,” Dean said in a soothing voice. He leaned down and put his hand on the child’s back. “What’s wrong?” A crash of thunder sounded and Ben screamed, digging his face into Dean’s leg.

“Ben!” Lisa called, bursting into Dean’s cabin. She shook her head and walked over to grab her son. “I’m sorry, Dean, he’s just frightened by the storms.”

Dean smiled, “It’s okay.” Lisa knelt down to try and pry Ben from Dean’s leg, but the kid only screamed and held onto Dean tighter.

“I’m really sorry for this,” Lisa said, sounding on the verge of tears herself. “He’s just trying to get used to life on the boat.”

“Lisa, it’s okay, really,” Dean said, putting his hand on her back. “You two can stay in here, if you want. I’m just doing some work. I don’t mind.”

Lisa looked up at him, “Are you sure?”

Dean shrugged and turned his attention to Ben. “Hey buddy, how about you let go of my leg?” He put his hands out and Ben immediately scrambled to cling onto them. “There ya’ go.”

“I don’t understand how you do that,” Lisa said, standing up with Dean. “My own mother used to try and hold him, but he would throw a fit.”

“Oh boy,” Jo said under her breath before speaking to Lisa. “Kids love Dean. Don’t know why, don’t know how he does it. But they do. Personally, I think it’s because Dean is a kid himself, deep down.”

Dean saw Lisa smile at Jo. “Really?”

Jo nodded her head and came over to stand next to Lisa. “You betcha. He cries easily, he’s needy, he’s constantly whining, and if he doesn’t get what he wants he’ll throw a fit, too.”

Lisa laughed, looking back at Ben with a smile. “I bet.”

Dean scoffed. “I don’t know _what_ she’s talking about. I never cry.” He brought his hand up to rub Ben’s back.

“Well, whatever it is, I’m glad it works on Ben, too,” Lisa said. She looked at Ben fondly.

“You can lie down if you want,” Jo said, pointing at Dean’s bed. “He doesn’t mind.”

Lisa shot her eyes between Dean and Jo, scrunching her eyebrows together. “Thank you.” She said, walking over to gingerly sit down on the edge of Dean’s bed.

Jo smiled, “Alright. I’ve got some work I’ve got to do. Wish me luck,” she said, tipping her hat and walking out. Another loud crack of thunder sounded; Ben didn’t scream but he scrambled to cover his ears while pushing his face into the crook of Dean’s neck.

“It’s okay, Ben,” Dean cooed. “I’ve got you. Nothing bad is gonna happen to you while I’m around.” He walked back over to his desk and sat down, humming a song quietly to Ben. One of the songs his mother would hum to him when he couldn’t get to sleep. All those years ago...

Almost ten minutes later, Dean could hear Ben’s breathing become even and his body become heavy. He was asleep.

“Dean,” Lisa spoke quietly, not wanting to wake Ben, “May I ask you a question?”

“Sure,” Dean said, standing up and walking slowly over to sit next to her. He gingerly laid down Ben next to him and smiled when Ben stretched out before scooting until his back was against Dean’s leg. “What is it?”

“Are you and Jo… together?” She asked, a slight catch in her voice.

Dean laughed quietly, “No, we’re not. At one point we were, but we realized our feelings are completely platonic.”

Lisa nodded. “I see.”

“Why?”

“Nothing,” Lisa said. She wouldn’t look at Dean.

“What?” Dean asked, shifting to lay Ben down on his stomach in the middle of his bed, still rubbing his back.

“I just… When I came to you that night they took Ben from me, I thought I saw…”

“Castiel Novak,” Dean finished for her. Lisa’s eyes shot to Dean’s.

“Yes,” She said quietly. “I thought it was just my imagination, and I was hoping that you and Jo were together so that I could just pass off the resemblance to my imagination. But…”

“It wasn’t your imagination.”

Lisa closed her eyes. “I wish it was.”

“What do you mean?”

“Dean… Ben and I finally have a home; a family that loves us,” Lisa sighed sadly. “What if Michael catches you and Castiel together? What if _anyone_ catches you two together?”

Dean shook his head. “That’s not going to happen. You don’t need to worry about us.”

“But what if you _are_ caught?” Lisa insisted, “What will happen?”

“I’ll be hanged,” Dean said it like it was nothing.

“You’ll be killed. And where will that leave us? Your crew?”

“Still on my ship.”

Lisa looked at him with an almost angry expression. “You would be dead.”

“Charlie would become captain. All you would have to do would be to never come to Heaven again.”

“Dean—”

“You’ll still have a home,” Dean interrupted her.

“But Ben won’t have a _father!”_ Lisa almost shouted. She immediately covered her mouth with her hands both because she didn’t want to wake Ben up, but also because she just said _Dean was Ben’s father._

“Ben’s father?” Dean asked, his eyes wide. He knew Lisa didn’t mean he was Ben’s biological father, but that didn’t lessen the weight of her words.

“I’m sorry…” She whispered. “I didn’t mean—”

“Ben thinks I’m his father?” Dean asked, not able to help the little smile forming on his face.

“He started calling you his dad a few weeks ago,” She told him. “I know it’s so soon, we just came aboard not even three months ago, but… He loves you.”

“He called me his dad?” Dean asked, he couldn’t believe it. He felt like a hole in his chest had been filled. “He called me _dad?”_

Lisa nodded, looking at Dean’s face and feeling like she was about to cry. “He was talking to me the other day about how he wanted to give _dad_ this leaf that had blown on board. I asked him who he was talking about and he just looked at me as if I had just asked the craziest question ever before telling me he meant you.”

Dean grinned, looking at the boy on his bed. “Are you okay with that?”

Lisa felt her eyes begin to shed tears. She smiled and wiped them away. “Of course,” She laughed. “If you are.”

Dean looked into her eyes. “Aye,” he said, “I am. Of course. I really am.”

Lisa smiled brightly for a second before her face crumpled. “He can’t lose you, Dean. He would be crushed.”

Dean was still smiling, “Lisa,” he started, taking her hand in his free one, “I can’t promise you nothing is going to happen to me. But I can promise you that I’m going to do everything within my power to be here for Ben. To be here for you.”

“Really?” She asked, hope in her voice.

“Really,” Dean responded, turning his head to look at the beautiful child on his bed.

“Thank you,” She said, squeezing Dean’s hand. “Thank you for everything, Dean.”

Dean didn’t look at her when he spoke. “Of course,” he whispered, watching Ben’s face. “I’d do anything for you and… And my... My _son_.”

~  ~  ~

_August 23, 1693_

A little over five months after Dean had left, Cas’s father went on another trip to Crowley’s kingdom. He spent a few weeks there, and came back madder than ever. Michael locked himself in his study right after he got back. He took a week to be alone with himself and didn’t let anyone but the maids come in with food or drink.

Then, he summoned Cas into his study and made him stand in the middle of the room for a good half hour before he broke the silence by standing up and pacing in front of his desk.

“This is shit,” Michael mumbled. He stopped momentarily to flick on the switch to his desk lamp to bring light into the darkening room. “Crowley is a monster.”

Cas was still standing in the middle of the room, shifting from foot to foot and watching his father warily. “I’m sorry, father,” Cas whispered, expecting his father to just glare at him. But the next thing he knew, his father’s hands were on his shoulders and pulling him down to violently knee him in the stomach.

“This is _your_ fault,” He said as Cas dropped to his knees. “You didn’t even show up to that meeting! Do you have any idea how untrustworthy that made me seem?! Crowley called me a goddamn cad! What the fuck does he know?!” Michael looked down at Cas and sneered. “Get up.”

Cas struggled to his feet, holding his stomach. “I’m sorry.” He coughed and wheezed. His legs shook and his knees felt like they were about to buckle.

Michael scowled. He threw his hands up and paced again. “That fucking bitch,” Michael spat. “This is her fault too. Abaddon's son — fuck! Tom has been exiled since he was thirteen! However that bitch got Crowley to even consider...”

Cas felt dizzy. He wasn’t able to get enough air into his lungs. The room started to spin as he gasped for breath. His lungs felt numb and something in his stomach was on fire. “Father,” Cas gasped, trying to tell him he needed help.

“You were supposed to be married to Meg right now. And Heaven wa supposed to have been taken into the Royal Kingdom.”

Cas felt like he was just hit in the stomach again. He had to have heard his father wrong. “What?” He coughed. Michael had never told him that that was what he wanted to happen between him and the King’s daughter. Cas thought they were just supposed to be business partners.

“Get the fuck out.” Michael snarled. “Get out of my sight.” He turned his back to Castiel. “What a pathetic excuse for a Novak.”

Cas stumbled out of his father’s study and down the hall, leaning against the wall for support until he found his room. He scrambled to get to his bed but ended up falling just short of making it. His knees crashed into the floor, his arms gripping the sheets while trying to pull him the remainder of the way onto his bed. His knees and stomach were screaming with pain.

“Cas?” The boy heard from somewhere far away.. “Oh my gods, Cas!”

He felt strong arms come around to lift him up. Cas whimpered, “Dean?”

“Yeah, baby, it’s me,” Dean said, kissing Cas’s forehead as he held the boy to him and slowly made his way down the side of the house.

“I can’t—” Cas gasped, “I can’t breathe!” He pushed his face into Dean’s neck. Dean jumped off the side of the house and a jolt of pain spread out through Cas’s body, emanating from his stomach. He bit the junction where the pirate’s shoulder met his neck to stop himself from screaming. Dean’s other arm came around him and he felt wind rushing past him and heard loud, quick steps being taken. Dean was running.

“What happened?” Dean asked, worry evident in his voice. “Was it Michael?”

Cas whimpered again, feeling like someone was taking a knife and stabbing him repeatedly and twisting the blade while they were at it. “Please,” He gasped, “Make it stop.”

“Hold on, Cas, we’re almost there. Gilda will fix you up.”

Cas clutched his stomach, “Please!”

“I’m so sorry, Cas, I’m so sorry,” Dean said, sprinting up the dock stairs to get to his boat. He took two at a time to get there faster. “Sam!”

“Dean!” Cas cried.

“Gilda!” Dean screamed, hurting his throat but not caring in the slightest. He swung himself and Cas onto the Impala and dodged people to get to the medical cabin. “Gilda, you in here?!”

“What-?! What’s wrong?” Gilda asked, “Oh my god!” Cas clutched onto Dean’s hand, whimpering for Dean not to leave as he was laid down on the examination table. Gilda grabbed a  pair of scissors and cut Cas’s shirt off. “What happened?”

“I-I-I — I don’t know,” Dean stuttered out.

“My father— ” Cas convulsed as a wave of pain shot through him. “—hit me in the stomach.”

“He did a lot more than that,” Gilda said under her breath. Dean’s head snapped to look at her.

“What is that supposed to mean?” He asked, his voice on the verge of tears.

“He just kneed me in the stomach,” Cas cried. “Please make it stop.”

“Okay, Cas, I need you to focus on my voice and tell me where it hurts the most when I press, can you do that?”

Cas nodded, squeezing Dean’s hand and taking as deep of breaths as he could without it hurting. Gilda pressed down under his rib cage on the left. Cas felt himself scream and lurch upwards. Dean held him down, looking at Gilda.

“What does that mean?” He asked.

“Ruptured spleen,” She said with a sigh of relief. “That’s an easy fix, but he needs to be put under.” Gilda pivoted around and then back in a matter of seconds. She held up a pill to Cas’s lips. “Take this.” He opened his mouth and swallowed.

“What was that for?” Dean asked.

“It’s going to make him fall into a coma,” Gilda said. Cas’s eyes widened. “Don’t worry, it’s better that way. I have to perform an operation of sorts, and it’s easier if you’re asleep.” Cas nodded his head, already starting to feel sleepy. “Once I’m done, I’ll give you a shot and you’ll wake up.”

“Dean,” Cas whispered, his hand going limp in Dean’s.

“I’m here, Cas,” Dean said, running his hand through Cas’s hair. “I’m here.

“Don’t leave,” Cas whispered, “I love you.”

Dean smiled, “I love you, too,” he said. Cas smiled and fell asleep.

~  ~  ~

“What’s wrong, Dean?” Sam asked, coming up to stand next to him.

“Cas’s father kneed him in the stomach, Gilda said it was an easy fix, but Cas needed to be put under. She kicked me out because she needs to be able to work with no distractions.”

“That’s promising,” Charlie said, appearing next to Dean. “She knows what she’s doing.”

“I told Cas I wasn’t going to leave his side.” Dean said, he began to fidget and look around.

“You’ll be there when he wakes up,” Sam said, “If Gilda said you needed to get out, then you don’t need to be in there right now.”

“You’re right,” Dean said, nodding.

“What happened to your neck?” Charlie asked, coming over to inspect Dean.

Dean shook her off, “Cas bit me when I jumped off his house. I was too far up, I should’ve gone down farther before jumping. That’s probably what made his spleen rupture.”

Charlie looked at him with a frown, “C’mon, I’ll fix you up.” She said.

“Thank you,” he said, following Charlie.

“I’ll stay here,” Sam called after them. Dean smiled back at his brother and gave him a nod. He was glad Sam was staying.

Dean followed Charlie to the kitchen, finally able to feel the pain setting into his muscles as he stepped into the mess.

Now, it was just Charlie and Dean in the kitchen at the moment. They were both on the floor, Dean had his back against a cabinet and Charlie was using a needle to stitch up the bite marks.

“You know Gilda is a fairy, don’t you?” Charlie asked.

“Yeah,” Dean said in a confused tone. On his ship it was common knowledge about Gilda.

“Well…” Charlie paused.

“What?” Dean asked.

“Have you heard of the old story about the Novaks being descended from Angels?” She asked.

“Yeah, everyone does. It’s a well known myth.”

“Gilda didn’t want to tell you until she was sure… but it may not be a myth,” Charlie sighed.

“What is that supposed to mean?”

“Gilda can see auras,” Charlie stated and Dean nodded. He’d stopped being surprised by Gilda’s hidden talents long ago. “Most humans have earthy colors - ones that only happen in nature. And aura’s don’t glow, per say. They’re rather… Neutral, dull; basically: not shiny.”

“So?”

“Cas’s aura…. It’s not… It’s shiny.”

Dean blinked, “What does that mean?”

“Gilda thinks the stories about the Novaks and angel’s is true,” Charlie said. Dean was stunned.

“He’s… He’s an angel?”

“No,” Charlie shook her head. “Not completely. She’s seen it with his uncle, too. Gabe’s aura is not as shiny as Cas’s, though. She thinks Cas’s got more Grace than any other Novak since the archangel, Michael.”

“It would make sense,” Dean said, “With Cas’s healing abilities, too.”

Charlie looked in his eyes and nodded. “It would,” She said. Dean smiled and shook his head, wincing when he felt the stitches pull at his skin. “Don’t move your head, idiot.”

“Sorry, I just…” Dean started. “I knew there was something different about him.”

“I’m sure you did,” Charlie muttered before grabbing a pair of scissors and cutting the nylon suture thread Gilda had invented. “All done.”

“Thank you,” Dean said. “I’m gonna head back and wait until Gilda’s done.”

“Nope,” Charlie said, “You need to go to sleep. And when you wake up, Cas will be okay.”

Dean smiled, nodding and beginning to stand up with Charlie before he stopped and looked at her with a concentrated expression. “We need to do something to get his father out of town again. At least for a few days,” Dean said.

“We can send him a letter from Crowley saying he wants to meet again?” Charlie suggested.

“Perfect.” Dean smiled. “Can you have Kevin write the letter and one of the swabs — Chuck or Becky, maybe? — can deliver it.”

“Will do, Captain,” Charlie saluted. She grabbed the bandages from the counter and placed one over Dean’s neck before patting him on the shoulder and walking out to give Kevin his task.

Dean leaned against the counter behind him and sighed.

“You want me to make you a pie?” Benny asked, appearing in the doorway and startling Dean.

“Fuck, Benny, don’t do that,” Dean said.

“Sorry.” Benny walked over to the fridge and began pulling out ingredients to make a pie.

“You don’t have to, Benny,” Dean spoke, shaking his head. “I was actually about to go to sleep.”

“Okay,” Benny nodded, he didn’t put away the supplies though.

“What are you doing?” Dean asked, watching Benny.

“I’m making a pie,” he said. Dean squinted at him.

“Why?”

Benny rolled his eyes, “‘Cause you’ll probably want one tomorrow. Or the next day, or sometime in the future.”

Dean felt himself smile. “Thanks, Benny.”

Benny looked at him from the corner of his eye, “Of course.” He smiled, too. “Now go to bed. I think Lisa and Ben are in there right now; sleeping, actually.”

Dean nodded and headed out, walking at a slow pace into his cabin and smiling when he got in there and saw Ben curled up against Lisa’s side. He changed into a nightshirt and pants before crawling under the covers and scooting closer to the Braeden's.

Ben stirred and sat up, looking around before yawning and lying back down with his back against Dean’s chest and his hand clutching his mother’s fingers. Dean sighed and closed his eyes, loving the warmth he got from having Ben next to him.

~  ~  ~

Cas groaned as he felt himself waking up. “Dean?”

“Hey, baby,” Dean whispered, coming over to grab Cas’s hand and kiss his forehead. “How do you feel?”

Cas turned his head towards Dean, not opening his eyes just yet. His head was throbbing and his stomach felt numb. “Thirsty.” He heard Dean laugh quietly before a cup was placed at his lips. Cas opened his mouth and gulped down the water until the cup was empty and Dean pulled it away.

“Better?” Dean asked, putting his hand in Cas’s hair.

Cas nodded, finally opening his eyes and finding Dean. He smiled lazily at the pirate. “You’re so beautiful.”

Dean chuckled again, “Thank you,” He pecked Cas’s forehead. “Looks like the pain medication Gilda gave you is working.”

“No,” Cas said, “The medication isn’t talking right now; I’m talking.” Cas’s words were slurred and came out slow.

“Okay, angel,” Dean whispered, “You want some more water?”

Cas shook his head, making himself dizzy. He groaned, closing his eyes and squeezing Dean’s hand. “I want to not be dizzy.”

“Okay,” Dean nodded, he stilled Cas’s still lolling head and turned it to the side for him; he smiled as they boy let out a small content sigh. “I’m glad you’re okay.”

“‘M too,” Cas murmured. Dean could tell he was falling asleep again. And he was okay with that. Cas needed his sleep. But they boy started frowning and trying to lift his head again.

“What’s wrong?”

“‘M fallin’ asleep,” He whined. Dean had to stop himself from laughing at how drugged Cas was at the moment.

“It’s okay,” Dean whispered, “You should go to sleep. The drugs will wear off.”

Cas pouted, turning his head to the side. “No,” he muttered, sounding a little like a petulant child. “Wanna talk with you.”

Dean smiled, scanning Cas’s adorable face, “I’ll be here when you wake up,” he said, running his hands through Cas’s hair, earning a smile from his angel. “We can talk then.”

Cas hummed, “Keep saying words.”

Dean smiled wider, “Okay,” he whispered and moved to sit down on the edge of Cas’s bed as he started telling Cas about one of the old pirate stories that he’d heard when he was little.

Cas fell asleep with a dopey grin on his face and drool spilling from the corner of his mouth. But Dean didn’t stop talking to him, and he didn’t let go of his hand.

Dean was just finishing up his story when Gilda came in. “Did he drink his water?”

“Yeah,” Dean said, nodding his head and turning to look at the fairy.

Gilda smiled, “Good.” She came over to stand beside the bed to check Cas’s vitals. “Everything seems good.”

“You’re sure?” Dean asked, looking back as Cas, who still had a pleased smile on his face and drool coming out of his mouth.

“Have I ever been wrong before?” Gilda asked, giving Dean a look of loving annoyance.

“Not that I can think of,” Dean smiled.

“Charlie told me she talked to you last night about Cas being descended from angels,” Gilda said quietly. Dean nodded, not taking his eyes off of Cas. “What are you thinking?”

“I think he’s perfect,” Dean said, using the edge of his sleeve to wipe away some of the drool on Cas’s cheek. “I couldn’t bring myself to care if he was half troll. I love him.”

“I know,” Gilda put her hand on Dean’s shoulder. “And he loves you, too. He’s dreaming about you right now.”

Dean felt himself smile wider. “Really?”

“Yeah,” Gilda said. She tilted her head to the side for a second before speaking again. “He’s dreaming about you and him traveling the world, raising kids, and growing old together. ”

“How many kids does he dream of us having?”

“Three,” Gilda said, looking at Dean for his reaction.

Dean brought Cas’s hand up to kiss it. “I think about that a lot, too.”

Gilda smiled, looking at Dean’s profile before tilting her head to the side and asking, “Why don’t you take him with us?” Dean felt his lips being tugged down.

“It’s too dangerous,” he said. “I can’t risk it. Not with him.”

“That’s not the real reason,” Gilda replied. Dean turned his head to look at Gilda.

“What other reason do you think I have?”

Gilda looked into Dean’s eyes, “You’re scared.” She said, “You’re scared that when you do take him with you that he’s going to wake up one day and realize he doesn’t love you. That he could do better than you.”

Dean scoffed. “Get out of my head.” Dean shook his head. “You’re using your powers. That’s not fair.”

“I can see people for who they are, Dean,” Gilda said quietly. “I can see through you.”

“Yeah? And what do you see?” Dean asked, a defiant tone to his words.

“I see a darkness,” Gilda started. “It’s very ugly—”

Dean cut Gilda off with a bitter laugh. “That’s why I think Cas can do better.”

“Let me finish.” Gilda scanned the side of Dean’s face again. “That’s on the outskirts of your aura. It’s not… _You._ It represents something that was done to you.”

Dean sucked in a breath, “Stop it.”

“Dean,” Gilda said in a firm voice. “You’re actual colors, they’re beautiful and big and vibrant.” She came to sit next to Dean, putting a hand on the side of his face. “Brilliant blues, greens, yellows and reds. There’s even some white.”

“What do those colors mean?” Dean asked.

“It means a lot of things,” Gilda started. “Blue is associated with stability, and symbolizes trust, loyalty, and confidence. Green symbolizes growth and hope. Red indicates courage, love, and power. White is rare. Cas’s aura is almost completely white; it’s angelic and it means goodness and divinity.”

“Do you think that comes from Cas?”

“I do, in some aspects. I don’t think all of it comes from him. I know some of it comes from you.”

Dean sighed and closed his eyes, “Thank you.”

“You’re not a bad person, Dean,” Gilda responded, standing up and pressing a kiss to the man’s temple. “You’re a person who has had horrible things done to him. And that’s not your fault. It was never your fault… You deserve to be happy.” She smiled at Dean and then walked out of the room.

“Dean,” Cas mumbled in his sleep, catching said man’s attention. He smiled at the boy and held his hand tighter.

“I’m here, baby,” Dean said softly, cupping Cas’s face, “I’m here.”

~  ~  ~

_August 24, 1693_

“Dinner’s ready,” Benny came into Cas’s medic room, finding Dean laying over Cas’s legs, fast asleep and snoring. He leaned against the door jam and smiled. Seeing Dean in love made him very happy. Dean deserved it.

“Hey,” Cas said, smiling and looking at Benny with blurry eyes.

“Morning,” Benny smiled, “Or, I should say evening.”

“How long have I been asleep?”

“Pretty much all day,” Benny responded. Cas nodded and looked down at Dean.

“Has he been in here all day?” He asked.

“Yep,” Benny laughed, “He didn’t want to leave just in case you woke up.”

Cas smiled at the pirate. “He didn’t have to do that.”

“He said he promised you,” Benny said, still smiling. Cas smiled back before stretching and yawning.

“You said dinner was ready?” Cas asked.

Benny nodded and said, “Aye, but I’ve made something special for you.” He pointed at the tray of food next to Cas’s bed. “Doctors orders.”

“Thank you,” Cas said, reaching over to grab the food. He shifted his legs and moved Dean, who snorted loudly before sighing and going back to snoring quietly. “He’s so handsome when he’s asleep.”

“He is,” Benny nodded in agreement. “He wasn’t always handsome, you know.”

“Oh, I very much doubt that,” Cas laughed, running a hand through Dean’s hair.

“Oh, aye; you best believe it. He didn’t used to be handsome. He used to be downright _cute.”_

“Really, now?” Cas smiled brightly and laughed.

“Absolutely. And when he’d wake up in the mornings, that’s when he was cutest.” Cas’s eyes came up to meet Benny’s for a split second, a brightness in them, before going back to Dean’s face. “But don’t tell him I told you.”

Cas smiled again and there was a soft giggle in his voice as he spoke, “My lips are sealed.” Neither of them spoke for a while. Cas watched Dean as he slept, and Benny watched Cas.

“He really does love you, you know?” Benny said.

Cas smiled to himself. “I love him, too.”

Benny knew Cas meant his words, but he couldn’t help the feeling of protectiveness that crept through his veins. “Cas,” Benny started, waiting for the boy look up at him. “Dean has been through a lot. He’s had to go through so many horrible things — things you couldn’t imagine. You have to be careful with him. He may not seem like it, but he cane fragile; and he needs protecting, too.”

Cas nodded his head, “I wouldn’t want to hurt him.”

“I know that,” Benny continued, “I don’t think you would want to hurt him; I just want you to know that he’s flawed, too, and he needs your patience. I assume you’ve seen the scar on his back?”

“Yes,” Cas nodded.

“Has he told you how he got it?”

“No,” Cas shook his head.

“That’s where you’ve got to be patient with him. You have no idea the horrors he’s had to live through,” Benny said. “And you have to give him time to confide in you with them.”

Cas nodded again, looking at Benny intently. “Of course.”

Benny felt himself relax, but only slightly. “I like you, Cas, but I need to make sure you’re not going to hurt Dean. He’s my best friend.”

Cas smiled at the man. “I admire that,” He said, “Thank you. I’m glad Dean has someone looking out for him.”

Benny smiled back at Cas, “Aye,” he said, nodding his head and pushing off the door jam. “I’ve got more food to attend to; if you don’t mind.” Benny came over and handed Cas a bag with what Cas assumed to be food for Dean.

“Thank you,” Cas said, taking the bag from Benny and waving as he exited. He set it on the table next to him and dug into his own food: mashed potatoes, creamed corn, and pudding. Everything was fantastic. Benny was honestly one of the greatest cooks he’d ever had the pleasure of being served food from.

Just as Cas was finishing, Dean started to stir. “Shit,” Dean groaned as he pushed himself up. “Gods, my neck.”

“Hey sleepy head,” Cas greeted, smiling warmly at Dean.

“Hey,” Dean said back, rubbing the back of his neck and looking at Cas with his eyes squinted. “How long was I out?”

“I have no idea, honestly. I just woke up about ten minutes ago.”

Dean chuckled as his eyes landed on the bag of food Benny had brought. “That for me?”

“Yeah,” Cas nodded. Dean leaned across Cas to grab it. He opened it and immediately dug into the food in it. “What’d he make?’

“I have no idea,” Dean said, covering his mouth while he talked and chewed his food. “But it’s really good.” Cas smiled at Dean and watched him as ate. He trailed his eyes to Dean’s neck and saw the bandage on the junction that connected his shoulder and neck.

“Did I do that?” Cas asked, pointing at Dean’s neck.

“Uh,” Dean hesitated, “Yeah.”

“I’m sorry,” Cas said, frowning. “My stomach was hurting so bad.”

Dean shrugged him off. “No, it’s fine. I’m just glad you’re okay. Everything is okay now,” Dean said, smiling. Cas smiled back and grabbed Dean’s hand.

“It is.”

“And it’s doubly okay because I’ve had Kevin write a letter up to your father from ‘Crowley’ asking him to come back right away to discuss some legalities.”

“Really?” Cas asked, his voice hopeful. Dean nodded, moving to sit closer to Cas.

“Yeah,” Dean responded, looking into Cas’s eyes. “He should be gone for a few days.”

Cas smiled, “Great,” he said, giving Dean’s hand a squeeze. “How long do I have to stay in here for?”

“Gilda said you should be ready to go tomorrow.”

Cas pouted slightly. “I wanted to sleep in your bed, with you, tonight.”

Dean laughed, “I can sleep in here with you, if you want?”

“This bed isnt big enough for both of us to lie down on,” Cas said. Dean scoped out the bed before standing up and pulling the covers off of Cas. He came back onto the bed and pushed Cas’s legs apart to settle between them and use Cas’s chest as a pillow.

“Does this hurt?” Dean asked, lifting his head to look at Cas.

Cas shook his head. “No, not at all. I like being crushed by you.” Dean laughed again, and began to shift himself off of Cas, but the boy stopped him. “That wasn’t sarcasm.”

“You like being suffocated by me?”

“You’re not suffocating me,” Cas rolled his eyes as he smiled. He bent his knees and wrapped them around Dean loosely. “I can still breathe. But I can feel your weight on me and it’s comforting.”

Dean smiled at him. “Yeah?”

“Yeah,” Cas agreed, running his hands through Dean’s hair. He heard the man sigh in content as he lightly scraped his nails along Dean’s scalp.

“I love you, Cas,” Dean said.

“I love you, too, Dean,” Cas responded. Dean moved his head to look into Cas’s eyes.

“I really love you,” He whispered, “There really aren’t any words, in any language, that could describe you exactly how much I love you… How much I’m _in_ love with you.”

“Me too,” Cas responded. He tugged on Dean’s hair, trying to get him to come up to kiss him. Dean got the hint and pushed himself up to kiss Cas.

They kissed until they were both breathless, and even after that they continued to press their lips against each other. Dean whispered the words ‘ _I love you_ ’ into Cas’s mouth with every kiss, and Cas gasped the same into Dean’s mouth.


	8. Chapter Eight

**Summary for the Chapter:**

> Dean finally tells Cas how he got the scar on his back.

**Notes for the Chapter:**

> Okay, Dean's past is not for the faint of heart. Some truly terrible things has happened to him and once you're done with the smut scene, if you don't handle sorta gorey suff well then just stop there. I'll post in the next update what all was discussed between Dean and Cas about Dean's past. 
> 
> TW: Abuse, rape, torture (all done when Dean was a child so it's in the past, but still.)

Chapter Eight

_September 2, 1693_

Dean started the conversation with Cas about him being descended from angels; with Gilda’s help, of course. Cas didn’t believe it at first. But then Gabe appeared, almost out of nowhere, and confirmed the claim. Apparently, Gabe had been researching this since he was a kid; it’s part of the reason that Michael hated him so much. Gabe was like Cas: he had more Grace in him than Michael. And Michael was not happy about that.

Regardless, Cas took his time to process the news; he didn’t want to think too much about it for a while. And in the meantime, he was as content as he could be under the circumstances. Seeing as though he was still _supposedly_ healing, Dean and he spent all their time together cuddling and kissing and talking. Even though Cas has been feeling completely better since the second day after the incident, Dean insisted he hadn’t even thought about going farther than shedding only their top layers. Cas had to admire Dean’s self control because on the flip side, he was just about to lose his mind.

Absolutely, yes; he _loved_ spending time with Dean and doing honestly anything other than making love, but he also loved feeling Dean fill him up so completely it ached in the absolute best way possible.

“What are you thinking about?” Dean asked, kissing Cas’s neck and running his thumb over the boy’s collarbone. They were lying together on Dean’s bed, Cas on his back and Dean between his legs — naturally — grazing his lips across Cas’s naked chest.

Cas sighed and took a minute to relish in the feeling of Dean’s lips on him. “Nothing,” he muttered.

Dean snorted, “Right, and I don’t love pie.” Cas smiled and giggled a little. “So, what were you really thinking of?”

“Not _much_ , really,” Cas blushed. “It’s just… Gilda gave me the all clear last week. Meaning, we can have sex, but we haven’t. And I’m starting to get frustrated because of it. It’s been two _weeks_ that we haven't had sex. I want…” Cas blushed and looked away before speaking again. “I want to feel you inside me.”

“I don’t want to rush into doing anything that’s going to hurt you again.” Dean said, his voice strained and a little hoarse. Cas realized that Dean was just as starved as he was.

 _“God,_ Dean, you won’t. Gilda gave me the okay a week ago. _Seven_ days ago. Any more time spent ‘recovering’ is just time I could be riding you.”

Dean lifted his head up to look at Cas. “Are you sure?”

Cas rolled his eyes before bucking his hips into Dean. _“Fuck_ me!”

Dean groaned as his elbows started to shake and almost give out. “Damn it, Cas,” he said breathlessly as Cas kissed his way to Dean’s neck and sucked a bruise into his skin. He grazed his teeth along the hollow of Dean’s throat and used his legs to roll him over onto his back.

Cas straddled Dean’s waist and grabbed the taller man’s wrists. He pushed them up onto the pillows and leaned down to growl into the man’s ear. “Don’t move them.”

“I love it when you take charge like that,” Dean said with a smirk. Cas slid down to undo Dean’s pants enough to get his cock out, immediately taking the head into his mouth and shaft in his hands. It was the most effective way of wiping the smirk off of Dean’s face. And while he was circling his tongue around the head of Dean's cock, he managed to get Dean’s pants and drawers off the rest of they way, tossing them onto the floor. “Fuck, Cas!”

“Mhm,” Cas moaned in response, making the older man gasp loudly.

“Shit,” Dean almost cried. Cas was bobbing his head and swirling his tongue around the head of Dean’s manhood furiously while twisting and pumping his hands along his shaft. “Fu-u-uck!” Cas felt himself smile around Dean’s girth. He bobbed his head for a few more minutes before pulling off and looking at Dean.

The man was breathing hard, biting his lip, and gripping the headboard so hard his hands were turning white. Cas smirked and crawled back up to Dean’s face. “You gonna fuck me now?” He asked, pushing his clothed length against Dean’s and making the older man’s eyes snap open.

Dean growled and surged up to pin Cas down on the bed with his body. “How do you want it?” Dean asked, licking a stripe from Cas’s collar bones to his jaw.

“I don’t care,” Cas gasped, trying to push his hips into Dean’s. “I just want your cock inside me.”

Dean laughed, “I don’t know,” he said huskily, nipping harshly at the spot where Cas’s jaw started. Cas arched his back into Dean and whined. “I think I’m gonna tease you. Teach you a little lesson?”

Cas whined in protest making Dean chuckle as he grabbed both of Cas’s wrists in one of his hands and pushed the other into Cas’s pants to take Cas’s member into his hand. He started pumping Cas at a slow pace. Cas closed his eyes and moaned quietly, biting his lip.

“Please,” he moaned, trying to thrust his hips into Dean’s hand.

“Where’s my bossy boy gone to?” Dean husked into Cas’s ear. Cas whined loudly as Dean let go of Cas's member, trailing his hand up to flick and pinch at the boy's nipples until Cas was writhing under him.

Dean sat up and leaned back to rifle through his bedside table; pulling out the oil and rope. He carefully manhandled Cas onto his stomach, tying his arms behind his back before jerking Cas's up onto his knees by his hips. Cas turned his head to the side and closed his eyes, his shoulders laying heavily on the bed.

“Dean,” Cas moaned as Dean roughly pulled his pants down to just above his knees.

“Sh,” Dean smiled, making Cas whimper pitifully. He leaned over, placing kisses along Cas's spine before moving to circle his tongue around the rim of Cas’s entrance. Cas jerked back against him, whining out a desperate plea for more. Dean smiled before pushing his tongue into Cas — as well as two of his fingers to rub against the spot that made Cas go crazy. The boy pulled on his restraints and cried out helplessly. He mewled and pushed back against Dean's mouth until Dean put his hand on his lower back, keeping him still.

Cas felt his cock ache between his legs and he wanted nothing more than to be able to touch himself or for Dean to reach down and jerk him off. But Dean was the one setting the rules right now. And Cas loved it, if he were to be honest. He loved when Dean dominated him; he loved being helpless to Dean. Part of it was because he knew Dean wouldn’t really hurt him, and he’d stop if it got to be too much. Cas trusted Dean with the most intimate and vulnerable parts of himself.

Dean crooked his fingers and sent Cas into a frenzy of incoherent babbling that soon turned into gasps and whimpers. It always amazed Dean how worked up he could get Cas in such a short amount of time. He made a mental note that one day he’d have to get himself and Cas cock rings so they could, quiet literally, fuck all night long.

“Dean!” Cas managed to get out. Dean turned his attention back to the whimpering mess before him and smiled.

“What do you need, baby?” Dean asked, pushing his fingers against the bundle of nerves inside Cas mercilessly. Cas felt himself getting close.

“I’m about to come!”

Dean paused his movements, drawing a wanton cry of denial from Cas. “Okay,” he said and pulled his fingers out of Cas’s hole.

“No, please! Please don’t stop!” Cas begged. “Please, I was so close!”

Dean smirked and oiled up his manhood before teasing Cas’s rim with the head of his cock. “You want me to just fuck into you?”

“Please?!” Cas shouted, futilely trying to push his hips back to take the man’s cock inside him.

Dean pushed the head of his cock into Cas, making him gasp and his thighs tremble. He draped himself over Cas. “Tell me how much you want it.”

“Please,” Cas whimpered and scraped his nails against whatever skin of Dean’s he could. “Please, I need it so bad.”

Dean reached down and ghosted his hand over the boy’s length. “You can do better than just ‘I need it so bad,’ Cas” He ground out. He slammed his hips into Cas’s and pulled himself back out in one swift movement. Cas cried out, arching his back into Dean and pushing his forehead into the mattress.

“Please,” Cas sobbed. “I need you, oh my god, I need you. It’s been so long since I’ve felt you inside me and you feel so _good!”_

Dean inched his hips forward. “Go on.”

“You’re so big and you fill me up so nice and full,” Cas gasped, tears starting to leak out of his eyes. Dean pushed in another inch. “You’re so perfect; you make me feel so good.” Cas was rewarded with another inch of Dean’s impressive length. _“No one_ can make me feel like _you_ do.”

“That’s what I want to hear,” Dean said, rewarding Cas by thrusting into him, slow and deep. Dean pushed himself up on one arm while the other came to grip Cas’s hair. He pulled the boy’s head up by his locks and fucked into him. “Keep talking.”

Cas moaned, long and low, as he tried to speak to Dean. All that came out was mushed together syllables and whimpers that sounded like he was telling Dean to go faster and harder; Dean wasn’t able to tell which.

“I like this pace we’re at now,” Dean said smugly. “If you want me to fuck you harder and faster, you’re gonna need to _beg_.” Cas sobbed in response as he dug his nails into the meaty part of his palm. Dean let go of Cas’s hair to hold Cas’s hips still as he continued his pace.

“Please!” Cas whimpered, arching his back further up. “Please!”

“Nay,” Dean growled and grabbed Cas. He tossed him to the head of the bed on his back. Cas was sobbing and gasping for breath.

“Please,” He begged. “Please, I need to come.” Dean raised an eyebrow at him as he tugged the boy’s pants and drawers off the rest of the way, grinning as he bent Cas’s legs at his knees and pushed them up to the boy’s chest. He whined and whimpered as Dean moved his limbs.

“Your cock is leaking so much,” Dean noted, pushing Cas’s legs apart to look at the boy’s red and angry looking head.

“Please,” Cas pleaded again, “Please.”

Dean leaned down and kissed Cas sloppily before letting go of the boy’s legs and reaching between them to guide his cock to rest against Cas’.

“Dean!” Cas keened as his eyes squeezed shut and he wrapped his legs around Dean’s hips, bucking wildly to feel as much as the man’s length as he could.

“Fuck,” Dean chuckled, pushing his hips down and thrusting. Cas almost screamed at the friction it caused.

“Yes,” Cas said breathily, “Yes, please, more!” He opened his eyes to look into Dean’s, surprised to see all the things he was feeling and more. Adoration... Love... Want... And maybe a little bit of lust. 

Cas felt his orgasm building and started making breathy little noises, never breaking eye contact with the man above him. Dean smirked and slowed his hips, pushing Cas’s hips down into the bed and keeping them pinned there by his own as he dragged their cocks together painstakingly slowly. Cas’s mouth fell open and he started to go limp under Dean.

This denial was almost too much for him. He wanted to come right now. And he wanted Dean to use him for his own pleasure. He wanted Dean’s cum to paint his skin so he could see and feel the evidence of Dean’s want for _him._ Cas started panting loudly as his thighs began to tremble.

This was torture. Beautiful, painful, and fantastic torture.

“You look so amazing, Cas,” Dean said, his voice deep and husky. “I love watching your face while we fuck. You make the most beautiful expressions I’ve ever seen.” Dean gave a harsh thrust of his hips, making Cas’s legs jerk open and a pained whimper to leave his lips. “Maybe I’ll have to fuck you good and hard in front of a mirror some day so you can see just how fucking pretty you are.”

“Please,” Cas whined as his release built agonizingly slowly.

“Maybe I’ll tie you up while I’m at it. Make you watch yourself get fucked,” Dean leaned down to growl into Cas’s ear. “I know you’d love that: to see yourself completely under my control. Completely helpless under me with my dick pounding into you and my hand on your cock.” Cas let out a desperate noise, a cross between a cry and whimper. “I wouldn’t let you come, though. No matter how much you begged and pleaded for me to get you off, I wouldn’t let you. Not until I came first.”

Cas felt the slow burn of his release just begin to bubble over. “Please!” He gasped, “Please!”

“Not yet,” Dean said, pulling away swiftly. Cas threw his head back and sobbed as Dean grabbed him again and pulled him up so his back was against Dean’s chest. “I’m gonna fuck you like this,” Dean promised. “I know you’re close, though. So I’m gonna have to calm you down.”

“No,” Cas pleaded. “Please just take me already. Just fuck me so hard I black out.”

Dean laughed in Cas’s ear. “You get such a dirty mouth when you don’t get what you want,” Dean whispered. “But that’d be too easy for you, angel. I want you to _suffer_ in the best way possible.”

“Please,” Cas lamented.

“Is that the only word you know?” Dean asked, a scolding tone in his voice. Cas bit his lip to stop the cry he was about to let out.

“No,” He said, trying to push himself back onto Dean’s cock, but had no luck.

“What other words do you know, then?” Dean teased, one of his arms threading themselves around Cas’s waist to pull him back against his chest firmer. The other going up to his hair and pulling his head back to expose his neck.

“Dean,” Cas begged again, almost to the point of coming no matter what Dean did. “I’m so close.”

“Then I guess I’m just going to have to leave you like this until you can calm down,” Dean began to pull away.

“No!” Cas shrieked, pushing back against Dean and making the man fall on his back onto the bed with Cas on top of him.

“Oh, you wanna come like this?” Dean asked, biting onto Cas’s neck lightly and sucking.

“ _I don’t care!_ I just want you to fuck me stupid,” Cas pleaded, moaning as he felt Dean’s tongue flick against his neck.

“Say the magic words,” Dean said, cupping his hands under Cas’s knees and pulling his legs up and apart.

“Please,” Cas heaved. Dean slid the head of his cock against Cas’s rim, “Please! Captain, please!”

Giving a sharp thrust before pulling away again, Dean bit down on Cas’s shoulder, making the boy yelp. “No,” He scolded, removing his hand from under Cas’s knee and grabbing for the oil to pour on his cock. When he was done, he lifted Cas’s leg back up and pulled them even wider apart, making Cas blush slightly at the position; if someone were to walk in right now, Cas would, quite literally, be on display for them.

“Please,” Cas whimpered, his eyes lolling back into his head.

“I wanna hear my name fall from those lips like it’s the only thing you know.” Dean growled.

Cas wailed, “Please fuck me, _Dean !”_

“That’s it,” Dean said, immediately slamming into Cas and fucking the boy mercilessly. He angled his hips to hit Cas’s prostate, making the boy scream Dean's name with every thrust. At this point, it _was_ the only thing he knew.

Cas was on the verge of coming when Dean stopped and pushed them both up onto their knees. Dean wrapped one arm around Cas’s waist while the other went to play with the boy’s nipples.

“How close are you?” Dean asked, taking a look at the boy’s cock. “Gods, Cas, it looks like you’ve already come.”

Cas shook his head, “I haven’t,” he panted desperately. “I haven’t.”

“That’s just precome?” Dean asked in disbelief. “Fuck!” The pirate’s resolve broke and he pounded into Cas with reverence.

“Dean!” Cas wailed, convulsing forward as he came, only being caught by Dean’s arms. He dug his nails into Dean’s abdomen as he was fucked brutally through his orgasm.

Dean slowed his hips before stopping and giving Cas’s cock a few strokes, milking all the cum he had to offer out. “Do you need me to pull out?” Dean asked, nuzzling Cas’s ear; he wasn’t able to answer. Dean smiled fondly and pulled out, drawing a broken moan from the boy’s chest.

The pirate gingerly untied his wrists and rubbed the light pink indentations from the rope and laid the boy down on his back.

Cas had to take a few minutes to collect himself before he could open his eyes and look at Dean’s own length, still hard and precome beading at the slit. He groaned as he tried to push himself up to help Dean take care of it, but Dean stopped him.

“Nu-uh,” Cas whined, trying to slap Dean’s hands away, earning a chuckle from the older man.

“Sh,” Dean whispered, leaning down to kiss away the tears of pleasure still sliding down Cas’s face. “You want me to come all over your pretty little cock?” He asked, reaching a hand down to pump over his shaft.

Cas inhaled sharply and moaned. “Yes.” His knuckles dug into the sheet beneath him, turning white from his death grip. He bent his legs up farther. “Please.” Dean moved so Cas could rest his legs over his thighs and stroked himself faster, looking at Cas’s blissed out face.

Cas’s eyes travelled down Dean’s flushed body and stopped to watch Dean as he pumped his hand over himself. Breathing hard and waiting for Dean’s cum to paint his flaccid cock, he moaned loudly in anticipation. He panted, looking up at Dean, who was looking at Cas like he was the only thing that mattered to him in the world.

“Fuck,” Dean groaned out, a pleased and relaxed smile graced his face as he came. Cas shot his eyes down to his cock as he saw Dean’s cum coat his cock.  

“Dean, _oh_ _!”_ He felt himself shudder a pained whine left his lips as his cock jerked up from his stomach and a small line of cum spurted out of his length.

Dean let out a strangled laugh, “Did you just — Was that — Did you just come again?” Cas whimpered in response, curling forward from the intense pleasure flowing through his body. Dean stroked himself as the last of his cum spurted from his tip and landed on Cas’s cock again. He closed his eyes, burying his head in Cas’s neck as the boy continued to convulse. “I’m gonna take that as a yes,” Dean mumbled, leaning back up to grab whatever article of clothing he could find on the floor to clean Cas up.

"Ah!" Cas yelped and spasmed when Dean touched his stomach with the cloth and whimpered as if it burned him.

“Sh,” Dean whispered, pushing his hand under Cas’s upper back and kissing the boy slowly as he finished cleaning up. “I go you.”

“Dean,” Cas whispered breathlessly, a small convulsion causing him to push into Dean with a moan. “Dean… Dean…” Cas repeated the man’s name as Dean finished wiping away all the drying cum. He put his hands on Cas’s torso and kneaded his muscles. Cas turned and looked at Dean. “I... love... you,” he said between breaths.

Dean smiled and kissed Cas. “I love you, too, angel.”

~  ~  ~

_September 3, 1693_

Cas woke up the next morning with pants on. He felt better than he had in months.

“Morning, babe,” Dean said groggily, rubbing his eyes and smiling at Cas.

“Morning, Dean,” Cas responded, placing his hands over his stomach and rubbing away some of the soreness. “I can do that for you?”

Cas looked at Dean out of the corner of his eyes and nodded. Dean smiled and shifted himself down on the bed. He lifted Cas’s legs, sitting between them before he laid them down over his, scooting up until Cas could feel Dean’s thighs against his butt. The pirate’s eyebrows came together in a concentrated look at he gently pressed down on Cas’s stomach, working his way over the muscles with the heels of his hands. Cas closed his eyes and stretched his arms above his head, sighing.

“I’m not hurting you, am I?” Dean asked, pausing his movements and looking at Cas; who shook his head and breathed in deeply through his nose. Dean saw the small smile Cas had on and a smile of his own formed while he went back to working the knots out of Cas’s stomach, rubbing over the smooth and soft skin that he loved so much. He kneaded his fingers into the muscle just under Cas's navel, pressed his palms into Cas's sides, and when he finally couldn't take it anymore he leaned over and pressed a kiss just below Cas's ribs.

A few minutes later, Cas was biting his lip to suppress pleased noises. Dean was too focused on Cas’s stomach and didn’t realize the effect he was having on Cas until Cas wasn’t able to stop the moan that fell from his lips.

Dean’s head snapped up to look at Cas, who had gone back to biting his lip. Dean smirked. “You don’t have to keep quiet for me, angel.”

Cas cracked his eyes open to look at Dean. He couldn’t help the smile that overcame his face. “Shut up.”

“You look really good like this,” Dean complimented him. “Happy, I mean.”

Cas felt himself blush, “Thank you.”

Dean smiled at Cas. “I love you.”

“I love you, too,” Cas echoed as Dean started his ministrations on Cas stomach again. The feel of Dean’s strong, calloused hands on his skin made him weak. He was in his own little utopia of just him and Dean.

“Why do you want to leave Heaven, Cas?” Dean asked, not taking his eyes from Cas’s stomach. “Other than your father, what reason do you have to leave? You have a life here, and a legacy you can inherit once Michael passes… Why would you give that up?” Cas didn’t respond for a minute or two. He wanted to collect his thoughts before answering.

“I don’t want the Novak legacy,” Cas started slowly, “I’m not a Novak.”

“You are a descendent of the archangels.”

“Yes,” Cas said, following along a groove in the wooden ceiling with his eyes. “But that doesn’t mean I have to be a Novak. Family doesn't mean blood.”

“You’re right,” Dean said, leaning over and placing a kiss below Cas’s belly button.

“Thank you,” Cas said. He took a moment to enjoy being in Dean’s presence. But he felt something nagging at the back of his mind.

Benny’s words about the scar on Dean’s back — the one on his spine — made Cas itch. “Dean…” He hesitated. “How did you get that scar on your back?”

Dean tensed, digging his fingers into Cas’s skin slightly. “Which one?”

Cas sat up and situated himself in in front of Dean before he timidly traced his fingers down the scar along Dean’s spine. He felt the man jerk away from him, just slightly. “You don’t have to tell me, Dean,” Cas said, “You don’t have to tell me anything you’re not comfortable with.”

Dean wrapped his arms around Cas’s waist and buried his face into the boy’s neck. “It’s… It’s not that I’m not comfortable telling you.”

“It’s okay, Dean,” Cas whispered, tugging on the short hairs at the nape of his lovers neck.

“I just…” Dean sighed. Cas circled his arms around Dean’s shoulders.

“You don’t have—"

“When I was four,” Dean interrupted Cas. “My mother died. It was a burglary gone wrong and this bastard named Azazel trapped her inside our house as it burned down. He killed her.”

“I’m so sorry, Dean,” Cas whispered, running his nails over Dean’s shoulders lightly.

“My dad… He didn’t deal with it so well,” Dean continued, “He would disappear for days at a time and come back with blood on his hands. I’d ask him where he’d been, but he’d just look at me for the longest time and give me the same answer each time: hunting.” Dean held tighter onto Cas as he went on. “A few months before I turned eight I started seeing this man follow me around almost wherever I went. It didn’t bother me so much; I figured he was someone who worked with my dad and was a little to into his job or some bullshit like that. But then… Two days before my eighth birthday, he knocked at out door and asked for my father. It was obvious then that he didn’t work with my dad... Either way, though, I went and got my dad while I made Sammy go down for a nap — he was still young, then; only four. I snuck back out to find out what the man wanted. He told my dad—" Dean had to stop to take a deep breath. “He told my dad he wanted to buy me.”

“What?” Cas asked, his hands tightening their grip on Dean.

“He said that he had been looking for a boy about my age. Turns out, he’d been watching me for a few years — wanted to make sure I was the right one, I guess.”

Cas felt his heart hurt, “Dean…”

“He told my dad to name a price. My dad did and… And I was his. Just like that...” Dean said, inhaling a shuddering breath. “The next day I was on a ship headed out to the man’s castle. I was alone and the man’s crew leered at as if I were a piece of meat. I was so scared. No one would explain to me what I was going to be doing for the bastard. I thought I’d just be a whipping boy or a fucking stable hand. But no,” Dean let out an almost hysterical laugh. “No that’s not at all what he wanted me for.”

Cas felt a sense of dread creep up his spine, “Dean,” he whispered, pressing his face into Dean’s hair.

“Alastair. That was the name of the man. He owns Castle Purgatory on an island called _Vorago Abominationes_. No one’s heard of it; but it’s there. You know what it means?” Dean asked. “It’s latin.” He paused and shook his head in spite. “Pit of Abominations,” he laughed bitterly. “It’s an island full of monsters; the scum of the earth.”

“I’m sorry, Dean,” Cas whispered so quietly he wasn’t sure if he had actually spoken.

“No one who goes there is innocent,” Dean continued. “And once you’re there… You become a monster yourself.”

“You’re not a monster,” Cas said forcefully. Dean inhaled again, ignoring Cas’s words.

“When we got to the island, Alastair had two of his men drag me into the dungeons. I thought for sure I was going to be a whipping boy. But once again: _no_ _.”_ Dean pressed his face further into Cas’s neck, using the boy in his lap to block out all the light in the room from his eyes. “He led the men dragging me down to another level of his castle. The only thing keeping the halls from being pitch black was the torches; there was no windows or anything to let the sun in…” Dean stopped. He wasn’t able to speak at the moment. Cas traced his hand over Dean’s scar again, drawing a shaky exhale from Dean before he continued.

“We got to a room at the end of the hall and I was strapped to a table in there,” Dean said, his voice starting to break. “Alastair was smiling. It was a sickening look on him. Everything is. He’s a damned demon.” He had to stop and collect himself again. “Alastair sent his men away and just… looked at me. I thought he was going to kill me; I thought he was going to do anything than what he actually did…” Dean trailed off, digging his fingers farther into Cas’s muscles. There would be bruises there when Dean let go of him, but Cas didn’t care. He was too focused on letting Dean get his story out. “H-he cut my… My clothes off.” Dean was crying now. “A-and then h-he…" He trailed off. Cas didn't need Dean to finish, though. Cas knew what Dean meant.

“Dean...” Cas whispered, his own vision getting blurry.

“He didn’t prepare me for it or anything,” Dean sobbed out a wrecked laugh, “And let me tell you, it fucking _hurt_ _.”_ Cas buried his face in Dean’s hair and cried. “I was there for nine years, Cas. _Nine_ years.”

“I’m so sorry, Dean,” Cas said, flattening his hands against the man’s back, away from his scar.

“Alastair spent a whole year digging that scar into my back,” Dean ground out. “Each day he would cut through whatever had healed. I’m pretty sure that there was never a time where a part of my spine couldn’t be seen. Alastair made sure to let me know it, too. He’d force himself into me harder and tear my skin open more with his fingers... He said it was anniversary present. Gave it to me on our fifth.” Cas pushed himself away from Dean only enough to pry one of the man’s hands off his body and place it on his own frantically beating heart.

“I’m sorry,” Cas whispered, pressing a kiss to Dean’s temple.

“He said I had the prettiest bones he’d ever seen.”

“Oh, Dean.”

“I’m not sure how I didn’t die at some time during that year…” He added as an afterthought before shaking his head and continuing. “Two years after that, when I was fifteen, that’s when Benny was brought in as well; another fucking anniversary present... Having Benny there was just a way to further torture me because he was only taken a handful of times in my place. I was Alastair’s favorite.” Cas pulled away from Dean to see the man’s eyes red and bleeding, “He made me a monster.”

Cas’s heart broke further. He took Dean’s face between his hands, “Listen to me, okay?” Dean’s eyes darted frantically between Cas’s before he nodded. “You’re not a monster.”

“Alastair—"

“I know what he did,” Cas interrupted. “What did _you_ do?”

Dean’s eyes flashed with pain. “I screamed and cried and begged for him to stop.”

“You _fought_ him.” Cas ran his hand through Dean’s hair. “You fought against the monster that _he_ was. That isn’t something a monster would do. That is something a _hero_ would do.”

More tears slid down Dean’s face as he made excuses, “I lost hope.”

“Do you have hope for the future now?” Cas asked. “For _our_ future?” Dean nodded, sliding his hand over Cas’s heart again. “So you didn’t lose hope.” Cas smiled, “You just misplaced it.”

Dean shook his head sadly. “I let myself become an object.”

“Maybe,” Cas whispered, “But only because of the circumstances you were forced into.” He rested his forehead against Dean’s. “But you know you’re not, don’t you?” Cas felt Dean nod his head.

“I… I love you, Cas,” Dean said, his voice breaking.

“I love you, too, Dean,” Cas responded, putting his hands on Dean’s face again. He heard the man let out a small breath of air before he grabbed a handful of Cas’s hair and crushed their lips together desperately.

“I love you,” Dean breathed out, not moving more than an inch away from Cas’s lips. “I love you, Cas.”

“I love you, too,” Cas whispered back. “ _I love you._ ”

**Notes for the Chapter:**

> Hey y'all! So sorry for how late this chapter is! I meant to get it up much sooner, but life got in the way. 
> 
> I want to warn you all, too, that the chapter after nine may not be up for quiet a while. My GED was moved to next month, so that means I won't be getting a new computer until after that and my computer right now is slow as heck. But I'm going to do my best to keep up. I'm so sorry I started posting this as such an awfully busy time in my life. :( But I really am going to try and keep up. 
> 
> Thank you for reading! And tell me how this chapter is, 'cause I feel like it's not very good. But... I'm not sure.


	9. Chapter Nine

**Summary for the Chapter:**

> Cas wants to tell Dean how much he means to him.

**Notes for the Chapter:**

> Okay, so, in the last chapter if you didn't read Dean's explanation of how he got his scar, here's the skinny: 
> 
> When Dean was eight years old, his father sold him to Alastair and Alastair took him to his Castle Purgatory on the island "Vorago Abominationes" (it's latin and it roughly translates to Pit of Abominations) and he made Dean his slave, pretty much. Alastair used Dean for whatever he wanted. Whether that be sex (although it wouldn't be consensual on Dean's part), torture, etc... Alastair used Dean for whatever he wanted. And the scar came from their fifth "anniversary" when Alastair cut open Dean's back down to the bone and then kept it from healing for almost a year. (So you can imagine how awful it looks.) That's the story behind the scar. 
> 
> But this chapter is pretty much all fluff! So, enjoy!

Chapter Nine

_September 3, 1693_

Dean had been acting differently. Not a bad different; but, different. He would hold Cas a little too tight, kiss him a little too long, or get a little too rough when they made love. Cas didn’t mind it, and it wasn’t abnormal for every few loving gazes or touches to linger. But for Dean to squeeze Cas’s hand in a death grip or to find any excuse to be next to him — to touch him, that was abnormal.

Cas started to worry. He started to think that Dean wasn’t telling him something, and it scared him. His mind would wander during the day and go to the illogical extremes. _Maybe he’s trying to work up the courage to end it with me… Maybe he’s dying… Maybe he’s leaving and never coming back…_

It wasn’t until the third week Dean was in port and talking with Kevin and Ash did Cas decided to talk to Benny and Sam about it.

“He doesn’t think he’s good enough for you,” Benny said.

“And he’s scared that you’re about to figure that out and not want to be with him anymore,” Sam finished.

“What?” Cas asked, taken aback. _How could he think that?_

“Dean is a complicated man,” Sam sighed. “He’s got abandonment issues like you wouldn’t believe. Our father… He was not a good man. I don’t remember much from back then, but what I do… Dean was treated like our dad’s slave. He wanted Dean to take the place of our mother for me. But he didn’t.”

“You saw him as a father figure,” Cas stated. “And that upset your father.”

Sam snorted, “You got that right. He was more of a father to me than John ever was or ever will be.”

“Calm down,” Benny interjected, giving Sam a careful look. The younger Winchester took a deep breath and nodded.

“Thank you,” Sam shot Benny a quick smile before turning back to Cas. “Dean was a punching bag for our dad until the day he was sold to Alastair. John took everything out on him. Our parents’ marriage was not good. I was only six months old when our mom died, so I don’t remember her like Dean does.” Sam paused to get his point across and only continued after Cas nodded to him. “After he and Benny got out of Purgatory, we bought the Impala and then we set sail. It was just us three, and I didn’t want to lose Dean again, so I usually bunked with him. He doesn’t know this, but he used to talk in his sleep.”

“Oh,” Cas couldn’t help but gasp. He knew where Sam was headed with this. There’d been a few times in the past weeks that Dean had woken him up by jerking his arms or legs and mumbling incoherent words. Cas would snuggle up into his side and talk him back to being calm, and then he would fall asleep again, too.

“He’d have night terrors and he’d wake me up by screaming for Alastair to stop. It was awful,” Sam’s voice had grown hoarse. “And that’s the thing about night terrors, you can’t wake up the person having them. Not for a while. He had to go through that every night; a lot of times, more than once.”

“Dean has been abused his whole life,” Benny started when Sam had to take a moment to collect himself. “For the first seventeen years of his life, he was only used by and for others. That won’t be something he’ll be able to get over for the rest of his life. With time, he’ll learn to deal with the ups and downs better and better, but that doesn’t erase what happened.”

“Cas,” Sam said suddenly, pulling the angel’s attention to him. “Dean is much better now. But, like Benny said, he’s not going to be able to just get over this.”

“This meaning the first seventeen years of his life,” Cas clarified.

“Yes,” Sam said, “Charlie and Gilda, Jo, Benny and I have done a lot to help him with everything he’s been through. But, he’s still got a ways to go.”

“Of course,” Cas said, nodding. “What do I need to do?”

“Be there for him, mostly,” Benny said.

“Get him to talk to you,” Sam added.

“He’s not going to start conversations about his past, so you’re going to have to help him,” Benny continued.

“How should I do that?”

“Well,” Benny started, “Your approach shouldn’t be the same as Sam, mine...” Sam and Benny shared a look. “Or anyone’s. It should just be you going to him and talking with him.”  

“What?” Cas asked. “What was that look for?”

“Nothing,” Sam said quickly. Benny sighed and leaned back against the counter behind him.

“I don’t know if Dean has told you about him and I…” Benny started, obviously not sure how to approach this subject. Benny opened his mouth to continue, but Cas cut him off.

“It’s…” Cas said, “Maybe it’s my Grace or something, but I figured you’d had something to do with his recovery…” Cas paused to find the right words. _Sex..._ the word echoed in Cas’s mind. “In that particular area.”

“Yeah,” Benny said, not looking at Cas.

“I get it, I mean,” Cas said in hopes of dissipating some of the awkwardness in the air. “You’re the only one who could really understand what he’d been through. I… I would’ve done the same thing, in your place.”

Benny nodded and lifted his head to look at Cas. “Of course.” Cas smiled at him before standing up and looking at the door.

“I should go find Dean and ask him to talk to me?” Cas asked, looking from Benny to Sam and back.

Benny hesitated, “Yes.” His face morphed into a look of deep thought. “But you also need to be patient with him. Push him to answer you, but don’t force him over a bridge he’s not ready to cross.”

“How will I know if he’s ready or not?”

Sam huffed out a laugh, “You guy’s have a bond,” he said.

“Well, you have a bond with him, too,” Cas replied, a little bit of guilt settling into his nerves. Sam and Benny shared a look and Sam smiled.

“You and Dean do share a more profound bond,” he said, “More than anyone I can name.”

“It’s true,” Benny agreed. “He’s let you know him much more than anyone on this ship.”

Cas felt himself blush. “Thank you,” he said before a feeling of guilt set in. “And…” Cas sighed. “I’m sorry.”

“Sorry?” Sam asked, confusion clear in his voice and on his face.

“For what?” Benny finished the question.

“You guys have known him much longer than I have,” Cas explained, fidgeting with the sleeves of his coat. “I feel like I’ve taken something from you.”

“You haven’t,” Sam laughed a little. “I’m _glad_ you’ve come into Dean’s life.”

“Honestly?” Cas asked, feeling the corners of his mouth pulled upwards.

“Yeah,” he said. “Dean’s been happier since he met you.”

“Aye,” Benny agreed, standing up as well and walking over to Cas to clap him on the back. “He’s changed.” Cas smiled; he felt as though something inside him had been stitched together after being broken for so long. The word whispered itself in his head: _family_.

“Thank you,” Cas said, looking from Sam to Benny. “Really, you have no idea how much that means to me to hear you say that.”

“You’re part of the family,” Sam said, smiling back. “You’re a pirate at heart.”

“Aye,” Benny agreed.

“Now,” Sam said, “You should go see Dean; he should be done talking with Ash and Kevin by now.”

Cas nodded, taking a few step backwards out of the kitchen. “Thank you,” he said one last time before turning and walking briskly out into the mess and then onto the main deck.

Dean greeted not a moment later, “Cas!” He came over and gave Cas a big hug.

“Hello, Dean,” Cas said, smiling and closing his eyes as he inhaled Dean’s scent.

“How are you?” Dean asked, giving Cas a peck on the lips. “It’s only been a day, really, but I missed you.”

“I missed you, too,” Cas said, putting his hand on the side of Dean’s face. He looked into the taller man’s eyes and smiled. Dean smiled back and gazed into Cas’s eyes with love. If Cas didn’t know Dean as well as he did, he wouldn’t have been able to see the glimmer of worry flashing through his eyes, though.

“Let’s go to your room,” Cas said, taking Dean’s hand in his and pulling the man with him as he walked into the cabin’s hallway. “I have some things I want to say to you.”

Dean laughed, gripping tighter onto Cas’s hand ever so slightly. “Okay,” he said. “Should I be worried?” Cas breezed into Dean’s room and closed the door behind him before pulling Dean over to their bed. “I’m gonna take that as a no, then,” Dean said, melting into the bed and pulling Cas flush against him. Cas wrapped his arms around Dean's neck and smiled. Dean smiled back and kissed him slowly, smiling maybe a little too much for it to be considered a real kiss. He chuckled under his breath, pulling away and kissing down to Cas's neck.

“Dean,” Cas protested, “These aren't exactly the conditions I was hoping for when I said I wanted to talk to you.”

“It's not my fault you're so alluring,” Dean responded, his voice light and airy. He placed a final kiss to the hollow of Cas's throat before coming back up to be eye level with Cas. "What was it that you wanted to talk to me about?"

"It's not exactly a light topic, Dean," Cas said. Worry flashed through Dean's eyes and Cas immediately backtracked. "I want you to know that you're enough.” Dean's face fell.  

“I—” 

Cas cut him off, “You’re more than enough for me.” He reached up to cup Dean’s cheek. “You’re no where near _not_ being enough for me. You’re so far past being enough for me it blows my mind. I love you so much, and I hate that you think you’re not worthy of love.”

“Cas… I—”

“I know what you’re going to say,” Cas interrupted, leaning forward to brush his nose against Dean's. “Don’t.”

“I love you,” Dean whispered.

Cas smiled, “I love you, too.”

“I’m… I’m sorry I’m so hard to love sometimes,” Dean closed his eyes, leaning into Cas’s hand.

Cas whispered back. “You’re not hard to love.”

“I just…” Dean trailed off, not entirely sure what he was trying to say.

“You’re not hard to love,” Cas insisted. “It’s hard to get you to accept that you’re loved.” Dean buried his face into Cas’s neck. Which was easily becoming one of his favorite parts of Cas’s body.

“I’m sorry,” Dean said, close to tears. Cas kissed his temple and rested his cheek against it.

“You don’t have anything to be sorry about, Dean,” Cas whispered. He ran one of his hands down Dean’s back. “I just want you to know that I love you, Dean.”

“Thank you, Cas,” Dean breathed out. He kissed Cas’s neck, and slid his hands under Cas, splaying them on his back.

“I know it’s hard,” Cas said, scratching Dean’s back soothingly for a few moments before he continued. “Trying to accept other’s love when you don’t love yourself…”

“It’s the hardest thing ever,” Dean whispered. Cas nodded.

“Yes,” Cas said, “It is. But maybe that’s why I was put in your life: to help you learn to love yourself.” Dean let out a shaky breath as Cas continued. “Dean, you’re amazing. God, you’re wonderful. Look at how many people you’ve saved. Everyone on this ship is here because you helped them out of a tough situation.”

“I love you,” Dean whispered, clutching Cas as if his life depended on it.

“Charlie’s family had kicked her out,” Cas said, turning his head to speak into Dean’s hair. “Gilda was being abused, Kevin was being hunted, Ash was being forced to abuse his gift, Sam was with your father, Benny was in Purgatory, and you, Dean… You saved yourself, too. You saved everyone on this ship in one form or another.”

“Even you?” Dean asked, his voice small and almost sounding childish.

“Yes,” Cas spoke, “You gave me a family. You gave me something no one else could.”

“I love you,” Dean repeated, kissing Cas’s neck again.

“I love you, too, Dean,” Cas responded. “I love you so much.”

“Me too,” Dean lifted his head up to rest his forehead against Cas’s. “I’m so glad to have met you.”

Cas smiled, “Me too,” he echoed Dean. “Don’t ever forget that you’re all I want. Even if you’re doubting yourself when I’m not around to remind you. Don’t forget my words. Don’t forget that you’re the only one I want.”

Dean smiled back and nodded. “I won’t. I promise.”

“Good,” Cas said, tilting his head up to brush his lips against Dean’s. “I want you. I _choose_ to want you.”

“I love you,” Dean said, giving Cas a peck. “More than words can say.” Dean kissed Cas again, slowly and lovingly, taking both their breaths away before they settled down in each other’s arms, listening to the steady breathing of one another.

 _Happy,_ echoed through their heart and soul.


	10. Chapter Ten

Chapter Ten  
_September 12, 1693_

Cas looked up at Dean. “When’s your birthday?” He asked. Dean also looked up, an amused expression on his face. They were in the mess, having a midnight snack of cherry pie together.

“January twenty fourth,” Dean responded, putting another forkful of pie into his mouth. “Why?”

Cas scrunched his nose, “You really shouldn’t talk with food in your mouth,” Cas said, smiling still. “And I was just curious.”

“It’s past already,” Dean said, swallowing his pie before shoving another bite into his mouth.

“No, really?” Cas said, rolling his eyes and smiling. “I thought it was next Thursday.”

Dean smiled back, “Sarcasm,” he said. “Sass.”

“Absolutely,” Cas agreed, nodding. He watched Dean put yet another bite of pie into his mouth. “You’re twenty seven now, then?”

“Aye,” Dean responded, pushing all the pie in his mouth to one side and speaking out the other.

“You should’ve told me. We could have celebrated it.”

Dean shook his head, “I don’t really celebrate my birthday.”

“I bet I could’ve made it really...” Cas paused, making Dean looked up at him curiously. “...special for you.”

Dean smirked at him, “I don’t doubt it.”

“Next time?” Cas asked. Dean gave it a thought.

“I don’t know,” he said. Cas tilted his head to the side in thought.

“It’s alright if you don’t want to, of course,” Cas said. “I won’t force you to do something you don’t want to.”

Dean nodded, looking down at his now empty plate. “I don’t really like my birthday.”

Something clicked for Cas then. He reached across the table and took Dean’s hand in his own. “I understand.”

Dean squeezed Cas’s hand.“Alastair used to always give me a ‘present’ on my birthday,” he whispered, “Kinda took away the magic of the day.”

Cas nodded. “You don’t have to explain anything to me,” he said. “I understand.” Dean looked up at him and smiled thankfully. Cas smiled back and picked up his fork, stabbing his own pie and lifting it to Dean’s mouth. Dean chuckled and leaned forward to take the pie offered to him. But Cas giggled as he quickly moved his fork to the side, smearing red across Dean’s cheek. “You got some cherry on your face,” he said playfully, putting his fork down. Dean smiled at Cas deviously as he pushed his chair back. Cas did the same, grinning at Dean and keeping a close eye on him.

“Oh, _do_ I have some cherry on my face?” Dean asked, stepping around the head of the table as Cas backed away. “I wonder who put it there?” Dean smirked and lunged to grab Cas.

“No!” Cas squealed, laughing as he ran away and weaving between tables and chairs in the mess. He was hoping that with being smaller and more lithe than Dean, he could throw the man off his balance by zigzagging around the tables. But he’d forgotten how graceful Dean always was with his movements and a moment later, he felt Dean’s arms wrap around his waist and spin him around to lay him down onto his back gently on a table. Cas laughed and bent his knees up to frame Dean’s waist as his wrists were pinned above his head on the table beneath him.

“Gotcha,” Dean said, smiling at Cas.

“Only because I let you,” Cas said with a roll of his eyes for emphasis.

“Right,” Dean laughed, “That’s the only logical explanation.”

“Exactly,” Cas said, nodding. Dean let go of Cas’s wrists and slid them down to the boy’s hips, tugging at the hem on the button up shirt Cas was wearing.

“Well,” Dean said, flicking his eye down to Cas’s mouth and back up to his eyes. “Either way, someone is gonna have to clean this sugary crap off my face. And I don’t plan on doing it myself.” Dean pushed his hands under Cas’s shirt.

“I think I can help with that,” Cas said quietly, moving his hand to drag a finger through the _‘cherry goodness’_ — as Dean called it earlier that night — on Dean’s face. He brought it to his mouth and smiled when Dean’s eyes darted down to watch him suck his finger clean.

“I bet you can,” Dean said, as an afterthought. He promptly pushed his hands further up Cas’s shirt, stopping to flick his fingers across the boy’s nipples.

“Dean,” Cas gasped, arching his back just slightly. He reached his hand up to fist in Dean’s hair and pulled his head to the side. Cas lifted himself off the table enough to lick away the remaining cherry filling on Dean’s cheek before moving his legs around Dean’s waist to pull the man into him. Dean smiled, running his thumb across one of Cas’s nipples. Cas pushed his chest into Dean’s hands again and closed his eyes as Dean pressed his lips to Cas’s.

Dean plunged his tongue into Cas’s mouth as soon as he was able to, tracing along the backs of Cas’s teeth. He could still taste a hint of the bitter and sweet cherry filling from the pie. It was intoxicating and all Dean wanted to do was keep tasting that as well as Cas’s own mouth.

“Can’t breathe,” Cas gasped, turning his head away.

“Just as good as that pie,” Dean said, licking his lips. “Maybe even better.”

“Shut up.” Cas pulled the man down by the back of his neck into a kiss. Dean buttoned Cas’s shirt back up as they explored each other’s mouths with their tongues.

“You know,” Dean said into Cas’s mouth. “I do think you taste better than cherry pie.”

“You’re such a sap.” Cas pushed Dean’s head down to his neck. “Now mark me?” He dug his heels into the back of Dean’s thighs. Cas could practically feel Dean’s smirk against his skin. He alternated between sucking, licking, and kissing into the skin until a red blotch turned purple.

“How long do you think until that heals?” he asked.

Cas ran his hands through Dean’s hair, relishing in the feeling of Dean’s lips against his skin. “I can feel it starting to heal itself already, but Gabe has offered to help me control it better so I can keep your hickeys for as long as I want.”

“Really?” Dean asked, pushing up Cas’s shirt to take a look. “That’s nice of him.”

“Yeah,” Cas said, craning his head to look at Dean with a smile. “He taught me a few tricks on how to use the Grace I have to my advantage, already.”

Dean smiled and came up to be eye level with Cas. “I love you, you know?”

Cas blushed just a tiny bit and looked into Dean’s eyes. “I know. I love you, too.”

“I can’t say it enough or with as much meaning as I want it to have,” Dean continued. He pulled Cas up into a sitting position, standing between the boy’s legs. “I love you so much.”

Cas grinned as he brought his hands up to cup Dean’s face. “I know.” He pressed a loving kiss to Dean’s lips and felt the man’s strong arms come around his waist. “I love you, too, Dean. More than words can even begin to express.”

Dean rested his forehead against Cas’s, just wanting to feel the angel that he got to call _‘mine.’_ “Damn,” he chuckled, “When we get married it’s gonna be hard to write vows. I won’t have the words.”

Cas pulled away from Dean with a raised eyebrow. “‘ _When_ we get married’?” he asked. Dean’s face paled and he smiled nervously, showing his teeth.

“I-if you want to,” he said, looking into Cas’s eyes. Uncertainty clouded his confidence. “We don’t have to get married — of course — I mean, _if_ we get married. _When_ I take you with me some day. _If_ you want to, of course, you know.”

Cas continued to look at him with an amused grin. “You’re cute when you’re nervous.”

Dean rolled his eyes lovingly, “Okay,” he said. “I see what you did there.” Cas laughed and slid his arms around Dean’s neck. “Very funny.”

“I thought so,” Cas said, smiling even more.

“My sides hurt from laughing so much,” Dean said sarcastically, smiling just as much as Cas. “C’mon, let’s go to bed?” Dean helped Cas hop off the table and they walked hand in hand to Dean’s cabin. They helped each other undress and redress into their sleeping clothes before Cas pulled back the covers as Dean went to turn off the lights. In the darkness, Dean found his way back to Cas and crawled into bed next to him, pulling him close and holding him there.

“It’s when, though,” Cas said, giving Dean a peck. “ _When_ we get married.”

Dean smiled at him in the dark. “Really?”

“Yes,” Cas said. Dean’s heart filled with emotion before he crushed his lips against Cas’s and hugged the boy tightly.

“I love you,” Dean said between kisses.

“I love you, too,” he breathed out, running his hand through Dean’s hair.


	11. Chapter Eleven

**Summary for the Chapter:**

> Three months after Dean's left, Cas in confronted by a woman from the Novak kitchen staff. Ava tells Cas that if he doesn't get her onto Dean's ship and a place in his crew, she's going to expose them and their relationship. 
> 
> Luckily, Dean gets things under control and takes care of Ava.

**Notes for the Chapter:**

> Hey, everyone! I finally got my mew computer so I'm going to try and get to posting more and more frequently. I've written up to the fifteenth chapter and I'm about ten chapters away from finishing this fic. So, stay tuned!

Chapter Eleven

_September 16, 1693_

 

“Told you...” Dean huffed into Cas’s ear, “...I have stamina.” He punctuated his sentence with a sharp thrust of his hips.

 _“Oh!”_ Cas whimpered, raking his nails down Dean’s back. Dean chuckled and snapped his hips forward again, pulling out slowly before repeating his actions: fast in, slow out.

Cas had been on the brink of orgasm for the past _hour_. And for another half hour before that Dean had been slowly thrusting into him at a teasing and unsatisfactory pace.

“Gods, Cas!” Dean groaned as the boy moved his hips down to meet Dean’s thrust. Cas scrabbled to find purchase on Dean’s back again, making him groan loudly.

“H-huh… H-how?” Cas asked, feeling the heat in his abdomen, not building or falling; just burning. Dean kept him there with every movement of his hips.

“Who knows,” Dean grunted, angling his hips. Cas arched his back and screamed out Dean’s name.

“Oh _please!”_

“Sh, baby, I got you,” Dean whispered. He lifted his head from Cas’s neck, “I got you.” Cas whimpered loudly and screwed his eyes shut. Dean smiled and jerked his hips forward, making Cas cry out loudly and snap his eyes open to look into Dean’s. “I got you,” he repeated, making Cas gasp for breath as he fucked into him again.

 _“Yes!”_ Cas cried out. “Right there!” He moaned brokenly and Dean lost the last bit of willpower he had to hold off his orgasm. Slamming his hips into Cas with reverence, he crushed his mouth onto Cas’s, slipping his tongue in for a second before he had to pull away to breathe.

“I love you,” Dean gasped against Cas’s lips. Cas screamed as his orgasm crashed through him, making his toes curl and his vision go white. “Fuck, Cas!” Dean grunted, following Cas in release, thrusting shallowly through his high. Cas curled into Dean, mouthing at his neck and whimpering.

“Oh,” Cas breathed, “Oh my gods… Dean, oh my gods...”

Dean slid his hand to the back of Cas’s neck for support, “How you doin’? You okay?” he asked, stroking Cas’s thigh with his other hand. Cas’s arms unwrapped from around Dean’s shoulders and he sighed deeply. Dean’s brow furrowed in concern and he asked, “Was that too much?”

“No, Dean,” Cas said, his voice barely above a whisper. “No… _Gods_... I love you.”

Dean chuckled, “I love you, too, baby.” He smiled as Cas sighed again and let his head fall back onto the pillow. Dean’s eyes widened and then a laugh bubbled in the man’s throat. “What?” Cas asked, his brow creasing.

“You have cum on your face,” he said.

Cas blushed a light pink. “Where?” Dean leaned down and licked along Cas’s jaw and cheek.

“Nowhere, now,” he smiled at Cas, looking at him with amused eyes. Cas blushed harder before beginning to defend himself.

“You kept me on edge for an hour!”

“It was way over an hour, Cas,” Dean shook his head. “It was closer to two hours, honestly.”

“What?” Cas gaped.

“Told ya,” Dean chuckled, smirking. “Your man’s got stamina.” He leaned down and buried his face into the crook of Cas’s neck.

“No kidding,” Cas breathed out, tilting his head to the side and baring his neck for Dean. “How come you don’t hold out that long every time?”

Dean laughed and kissed a line along Cas’s neck. “Because you feel really fucking good; it’s hard to control myself when I’m inside you. And would you really want me to take that long to come every time we make love?”

“Oh… No. That would be torture.” Cas shook his head a little. His breath caught when Dean teethed at his pulse point before speaking.

“Plus the noise you make is _music_ to my ears.” Cas grinned and blushed, bringing a hand up to run through Dean’s hair. “Helps to push me over the edge faster, squarely.”

“I love you,” Cas mumbled, pulling Dean’s head up to kiss him quickly.

“I love you, too,” Dean responded, rolling off of Cas and grabbing the towel he’d set on his nightstand to clean them up. He ran it down Cas’s torso and then folded it and threw it into his hamper.

Cas yawned, stretching his back before rolling over and looking into Dean’s eyes. “I’m so exhausted.”

“Me too,” Dean said. Cas opened his arms and Dean settled into them. He rested his chin on the top of Dean’s head.

“I really love you,” Cas whispered as Dean wrapped his arms around Cas and kissed his neck. Dean smiled lazily.

“I really love you, too,” he whispered, placing another kiss on Cas’s collar bone. “Night, Cas.”

“Goodnight, Dean.”

~  ~  ~

_September 17, 1693_

 

Cas groaned as Dean hugged him tightly. “I’m so sore,” he explained, making Dean chuckle. Cas smiled and wrapped his arms around the man’s neck, pushing his forehead against Dean’s before speaking, “Are you?”

Dean smiled and pulled away, “No. I feel really light, actually.”

Cas stuck his tongue out at Dean. “Lucky,” he joked, pecking Dean on the cheek. “I’m still exhausted, too.”

“I feel very alive at the moment,” Dean said, “Despite the circumstances.” A frown tugged at the corners of his lips. Cas cupped Dean’s face with his hands and ran his thumbs along Dean’s bottom lip. The man sighed and leaned further into Cas’s touch, his eyelids drooping closed.

“I love you,” Cas whispered, moving his thumbs out of the way to kiss Dean.

“I love you, too.” Dean breathed out a laugh, sounding close to crying. “I’m going to miss you so much, Cas.”

Cas smiled sadly against Dean’s lips, “I’ll miss you, too.”

“Oi! Dean!” Sam yelled, running down the dock towards them. “We have to go, sunrise is getting close, and Cas needs to get home before that.”

Dean inhaled shakily as he rested his forehead against Cas’s again. “Yeah,” he said, his voice barely above a whisper. “I love you, Cas. I love you so much.”

“I love you, too, Dean,” Cas said. He leaned up to give Dean one last kiss. Dean surprised him by pulling Cas into his body roughly and kissing him passionately. It was enough to effectively take both their breaths away.

Cas gasped and grabbed onto the collars of Dean’s jacket to pull him still closer together.

“Dean,” Sam said, his voice slightly annoyed. “C’mon.” Dean ignored him and held Cas as he kissed his way to the boy’s neck.

“Dean,” Cas said breathlessly. “You have to go.” Regardless, Cas still let his head fall to the side to expose more skin. Dean nipped at the spot where Cas’s jaw ended before moving down and sucking a bruise into Cas’s neck.

“Dean!” Sam tried again.

“Be there in a sec’!” Dean grunted and waved his brother off, nipping as Cas’s neck some more. Cas found himself moaning seconds later as Dean’s hand came to palm at the front of his trousers.

“Dean,” Cas gasped, “You — oh!—” he moaned. “You need to go. Sam’s right. Sun will be up soon.” Dean groaned, upset, before lifting his head back up to Cas’s and kissing him again.

“I love you,” He breathed out, moving the hand he had on Cas’s groin to his hip. “I’m gonna love you forever.”

Cas breathed hard, longing to feel Dean’s hand back on him. “You’re such a tease,” he joked, knowing he had to wait to feel Dean’s skin against his once again. “But I love you, too,” he said and pressed a kiss to one corner of Dean’s mouth. “I’ll love you for _always.”_ He pressed another kiss to the other corner of Dean’s mouth.

Dean smiled and buried his face in Cas’s hair as he hugged Cas — almost too tight. Cas hugged him back, blinking hard to keep the tears from falling. “I’m gonna be back soon,” Dean whispered.

“Soon,” Cas agreed in an echo, releasing Dean and smiling as he made his way back onto his ship. Cas held his hand over the middle of his chest, right here he kept the pendant Dean gave him, and continued to smile as the ship sailed away. “Soon…”

~  ~  ~

_December 17, 1693_

 

Three months, to the day, Dean’s been gone. This time was no different than any other time he’d left; yet it was also much, much different. Cas was missing Dean more than normal. And he didn’t completely know why.

He froze as he heard the tell-tale signs of his father walking into the kitchen. But he couldn’t turn around, or his father would know he’d been crying and he didn’t have a good excuse as to why at the moment.

“Castiel,” Michael greeted. “You’re up early.”

“I am,” he responded, trying to keep the fact he wasn’t turning around discreet.

“I’ve some good news,” Michael said suddenly. Cas heard him walking over to sit down at the table in the kitchen usually only the staff sat at.

“That’s great,” Cas said.

“Yes,” Michael said. “It is. Crowley has decided to consider a business proposal between you and his daughter in exchange for Heaven to become part of the Kingdom. I expect you to be ready to meet with him and his daughter sometime in the far future.”

“Oh,” Cas breathed out. He didn’t want to meet Crowley or his daughter. “Why the far future?”

Michael sighed, “I wouldn’t get your hopes up.” Anger laced itself into his words. “Crowley is a massive twat. I wouldn't put it past him to be doing this just to get a reaction out of me.”

“I’m sorry, father,” Cas said. Michael made a noise of acknowledgment as he shifted, tapping his foot on the floor.

“You’re acting odd, right now,” he said. “Why haven’t you looked at me?” Michael made a irritated noise. “I _am_ talking with you. Are you trying to disrespect me?”

Cas tensed, “No, not at all father, never.”

“Castiel,” his father warned. Cas looked around frantically, searching for an excuse. His eyes landed on a spice that had been bought the other day, not even opened, and he finally turned to look at his father. Michael took in his appearance and squinted at him questioningly.

“Have you been crying?” He asked. Cas shook his head, his body continuing to tense to the point of cramping.

“No,” he said, trying to force himself to relax. “I ate something with too much red pepper in it.”

“Who made it for you?” Michael asked, an edge in his voice. “I’ll have them reprimanded — I don't want them putting too much red pepper in anything they'd give to me.”

“Oh, no,” Cas shook his head. “I’m the one who put the extra pepper in it.” Michael gave his son a long look before standing back up.

“Alright then,” He said curtly. The brusque tone had Cas flinching, almost imperceptibly; but the corner of Michael's mouth twitched and Cas knew his father saw the effect he had over his son.

Michael turned and walked swiftly out of the kitchen. Cas sighed and dropped his face into his hands.

“I _have_ been crying,” he whispered to himself.

“Why?” A voice made Cas jump. He stared at the woman standing there.

“What are you doing in here?” He asked, looking past her to make see if anyone else was going to be coming in.

“I work here,” she explained. “It’s my _job_ to be in here.”

“Oh,” Cas sighed. “I’m sorry. I’m just a little on edge.”

“Why?” She asked, leaning up against the door frame.

Cas looked her up and down. “What’s your name?”

“Ava,” she said. “Are you going to answer my question?”

Cas blinked with wide eyes at her. None of the servants had ever really tried to engage with him before. “Uh…”

“Is it because _Dean_ is gone?” She asked, smirking. Cas reeled back.

“What are you talking about?” He asked, eyeing her and trying to keep his nervousness hidden.

“Cut the crap,” She said. “Dean Winchester. You know, _The Righteous Man_. The pirate your father wants dead.”

“My father doesn't care that deeply about pirates,” Cas said quietly.

“Please,” Ava said, brushing him off. “You do know the reason you father has been trying to get Heaven to become part of the Kingdom is so he can use their military powers to kill Dean Winchester and everyone on his ship, don’t you, Castiel?”

“What?” Cas asked, his throat going dry. It wasn’t a huge secret that Michael had a particular hatred for Dean, but he wasn’t aware that that was the reason Michael wanted Heaven to become part of the Kingdom. That news had him to the point of almost crying again. For once he was glad Crowley was a gigantic dick. “Who told you that?”

“Look,” She started, fixing a cold, steely gaze on him. “I won’t tell anyone you’re in a relationship with Dean; on one condition.”

“There’s nothing to tell.”

“Right,” she snorted. “That wasn’t you sneaking out of your room all those nights ago to get fucked six ways from Sunday by him.”

Cas squinted at her. “You followed me?”

Ava nodded. “Yup,” she stepped over to the table where Michael had been just moments ago. “And I don’t want to tell anyone, but I will if I have to.”

“What do you want?” Cas asked, glaring at her. She smirked.

“I want Dean to take me with him the next time he leaves from Heaven,” she stated. “I can’t take this shit town anymore.”

“It’s not up to me who joins his crew and who doesn’t,” Cas said.

Ava stared at him, setting her jaw and glaring as Cas with a dangerous and angry look in them. “Fine. Then I’ll start telling everyone about you two.”

“No one will believe you,” Cas said, his voice small.

“Doesn’t matter,” She said in almost a snarl. “Once your father got wind of the rumors he’d ban Winchester from ever docking here again. There go your little fuck-fests.”

“We don’t fu—” Cas started to protest her terminology, but thought better. The less she knew, the less danger he and Dean were in. “I don’t know what to tell you.”

“It’s easy, Cas,” Ava said, using his nickname. It sounded like a threat coming from her. “Just tell me that when Dean comes back you’ll get me on board. And then, you’ll convince him to take me.”

Cas stared at her. “I can get you as far as the dock,” he said. “But I can’t promise that he’ll let you onto his ship or into his crew.”

She frowned in pity and said, “Oh, Cas. You’re important to Dean and if I have to use you to get what I want, then I will.” Ava stepped closer to him, leaning against the island counter. “I don’t want to hurt you. But I will if I need to.”

“O-okay,” Cas said. He pushed himself away from the counter, ready to run.

Ava smiled, “Thank you. Now if you excuse me, I have food to prepare for you and your mother and your father.” Cas quickly scrambled away from her, his heart pounding in his chest. He couldn’t have Ava going around and telling people his and Dean’s business. He just couldn’t… If she did, and Michael found out, Dean wouldn’t be able to come back to Heaven — ever. Even if Michael didn’t believe the rumor.

Cas wouldn’t be able to handle that; he wouldn’t be able to truly live. If Dean wasn’t able to come back to Heaven… Cas knew he wouldn’t be able to stop himself from receding into himself to the point of just going through the motions.

 

 

“Dean,” Cas whispered into his pillow later that night. He was staring at the stone Dean gave him and praying to someone — anyone, at this point — to bring Dean back as soon as possible. The feeling of being alone was getting to be too much at the moment.

“Dean,” Cas started again, closing his eyes and clutching the stone to his chest. “I need you back as soon as possible. I need you here with me. I need your arms around me, and I need you to tell me everything is going to be okay because right now it does not feel like _anything_ is going to be okay.”

Cas sighed, closing his eyes and imagining Dean next to him, snoring into his hair and his legs tangled together with Cas’s. He imagined waking up to the sun shining through Dean’s window in his cabin and lighting up the pirates features so beautifully.

“I really love you, Dean… Sometimes it frustrates me so much that I can’t find the words to tell you how much you mean to me. I hate that I can’t hold you as we fall asleep together. I want to be with you every day, so I can kiss you and hug you and watch the sunset and sunrise with you. I’m in love with everything about you... You make me feel so adored and _worthy_ and safe and… And...” He trailed off, thinking of Dean as he fell asleep.

~  ~  ~

_February 9, 1694_

 

Dean heard a man’s shout for freedom sound from outside. He’d found an abandoned shack that was perfect for a home base while he and his crew stalked their next target. Dean had taken about a week to trail him and another week for Benny and Sam to get him alone and grab him. They were bringing the poor fool to Dean right now.

Judging by how loud the scream was, they were right outside. He smirked and continued to pick at his nails as the door swung open and in tumbled a man with his hands tied together behind his back and a sack over his head. “Well, well, well…” Dean said from where he was perched on a stack of hay. He swung his right leg back and forth as he flicked his eyes to see Benny and Sam forcing the man onto his knees. “What do we have here?”

“Let me go you bastards!” The man screamed, trying to shake the hands off his shoulders.

Dean jumped down from his spot, landing with a thud a few feet in front of the damned man. “P.T. Sandover?” Dean asked, stepping up to kneel in front of the man. He pulled the sack off his head and smiled menacingly. “Welcome, my name is Dean Winchester.”

Sandover’s eyes widened and he let out a feeble “No.” Dean stood up and walked slowly around him. Benny put his hand on his throat as Sam walked away to grab more rope, throwing it towards the ceiling and over one of the crossbeams. Sandover watched Sam closely as he came back and threaded the rope through the bindings on his wrists. “What do you want? I haven’t done anything!”

Dean laughed, “Oh, Sandover,” he started, putting his hand on his shoulder. “You know that’s not true.”

“Let me go!” He screamed, pulling on his bindings. Dean looked up at Sam and nodded. Sam nodded back and pulled the other end of the rope until the businessman was forced to stand up.

“Nope,” Dean said, “We can’t let you go. You’ve been summoned.” He threw the Demon Deal papers down at the man’s feet. “A lot of people paid a lot of gold for you to suffer. Apparently people were tired of getting their entire lives destroyed because of _one_ mistake.”

“Has anyone told you you’re a workaholic?” Sam asked, sarcastic disgust dripping from his words before they took on a venomous tone. “You’ve killed so many people, Sandover. Mothers who needed to feed their family had to watch their children die right in front of them. More than one family go to the point where they found their kids eating the others because of how hungry they’d gotten.”

“One ex-employee didn’t even make a mistake and you destroyed him. He filled out a form, and just one four looked a little like a nine and had you shelling out an extra hundred gold to a customer for their return order,” Benny said. “You fired him and made sure he didn’t get work anywhere else.”

“Gods,” Dean said, looking at the man. “Apparently you made a mistake, too, Sandover.” He sauntered around the man, before stopping in front of him and looking at him in disgust. “You’re fucking pathetic.”

“Let me go, _pirate_!” Sandover said, spitting his words into Dean’s face. Dean smiled as he wiped the saliva from his face, letting out a fake laugh.

“Look here, Sandover, we’re not going to let you go. You’re going to die,” Dean said bluntly. He turned to the right and walked over to the table he’d set up with all his torture instruments on. “But if it makes you feel better, you’re not going to die right away. Ian Johnston paid extra for that.”

“What are you are you going to do?” Sandover asked, his shaky voice betraying his heated gaze.

Dean pivoted slowly to look at him with a menacing smile on his face. “We’re going to give you what the people paid for.” He picked up the Heretics Fork and walked back over. “It’s getting late though.”

“What?” Sandover asked. Benny came up behind him and yanked his head back to expose his throat. Dean turned the fork around in his hand.

“Do you know what this does?” He asked. It was a piece of metal with a two pronged fork at each end. “See, what we do is,” Dean paused to unclasped the fork from the collar to wrap the leather around Sandover’s throat. “We put this around your neck, and then we attach the fork, and if you lower your head, you die. It’ll impale your chest or throat.”

Sandover tried to jerk away from Dean, but Benny held him still. “No! Stop! Get away from me!”

“No can do, you son of a bitch,” Dean growled, pushing his head back farther and securing the fork onto the collar. “Now you’ll know what pain really is.” Dean brushed past the man and grabbed his hat on the way out. “Have a nice night.” He heard some gurgled protests follow him, Sam, and Benny as the exited and locked the shack back up. None of them paid any attention. They walked together down a path that led to their camp. The shore was too far away for them to be able to stay on the Impala while they were docked at Ohio Island. The Sandover family had set up their company here over a hundred years ago and had continuously been growing their influence.

However powerful, he’d be dead within the next week, though. Many ex-employees and their families as well as current employees had made sure he’d be gone sooner rather than later. If you were to count up how many people the Sandover family line had screwed over in their time settled on Ohio, you’d have go into unimaginable numbers.

“What will we do if he kills himself tonight,” Sam asked, breaking the men’s silence.

“Then we burn him,” Dean answered, seeing the fire from camp getting bigger with each step. “Easy deal done and finished.”

“But we said he’d be made to suffer,” Sam said, taking long strides to catch up with his brother.

“Trust me, Sam,” Dean said, “He’s suffering now. He won’t be able to sleep, he can’t scream or cry out for help, he’s stuck.”

Sam nodded. “Whatever you say, Dean.”

“Whatever I say,” Dean repeated, clapping his brother on the back.

~  ~  ~

_March 8, 1694_

 

Cas was just getting home from observing a debate with his father. It had gone later than normal, and Michael was exhausted.

“You’re allowed to go straight to bed when we get home, Castiel,” Michael said, his voice loud and cutting as he broke the silence that had settled between the two Novaks as soon as they had gotten into their transportation.

“Thank you, father,” Cas replied. “It has been a rather long day.”

Michael nodded. “I’d say so, yes.” Cas didn’t know how to respond to that, but luckily they came to a stop and didn’t have to continue.

Michael stepped out and walked briskly into their house, ignoring Cas. Something Cas was actually thankful for once. He made his way up to his room quickly undressed and redressed in his nightclothes, getting into his bed as soon as he was in his dark blue shorts he only wore every few months. Today had been the rare kind of day where it got warmer throughout and hadn't let up yet. So cas had dug the shorts from the bottom of his closet, pulling them on quickly and then getting into bed even quicker. When Dean was gone, he found it easier to go to sleep as soon as he was allowed to. It made the days go by faster.

“ _Cas_ ,” Ava hissed from the corner of his room. Cas yelped in surprise. Covering his mouth, and hoping he hadn't been too loud, he looked at the woman.

“What are you doing in here?” Cas asked, he pulled his covers up around him, furrowing his brow. How long had she been there, watching him… The realization that Ava had probably been there, sitting in silence and watching him undress made his skin crawl. “Did you watch me undress?”

“You bet,” she smirked, dropping her eyes to Cas’s covered lower half. “Is it normal for guys to be so small?”

Cas glared. “What do you want? To threaten me again? I already told you I have no influence over how soon Dean comes back—”

Ava stepped forward, “He’s already back,” she stated, quirking her eyebrow up. Cas felt his heart pound in his chest.

“Really?” he asked, edging off his bed and stepping towards his door. He had his trench coat hung up on a rack next to the door he could grab if he needed to escape quickly. “Are you sure?”

Ava nodded, “Yeah. I saw his ship dock earlier today.” She strode over to him and grabbed his wrist with impressive strength. “Let’s go. You’re getting me on that ship.”

“I’ve told you before,” Cas started, trying to pry her hand off as she tugged him out of bed, “I can’t promise that he’ll take you with him. It’s not up to me!”

Ava smirked, “You seem to forget I have leverage, Cas.”

“Stop saying my name like that,” Cas snapped as Ava dragged him out of his room, letting him grab his trench coat, and heading down the stairs. Ava laughed quietly.

“What are you going to do if I don’t?” She asked rhetorically. “You have no power over me.”

“Let me go. I can walk on my own, thank you,” Cas snarked. Ava shot him an unsettling look as they made their way through the kitchen and out the back door.

“You can also run on your own,” She rolled her eyes. “I’m not stupid.” Cas grit his teeth and let her drag him the rest of the way to the docks. He could see Dean’s outline standing there talking with someone. Cas almost broke into a run, but thought better of it.

“Start walking faster,” Ava demanded. Cas didn’t hesitate to comply, wanting to get to Dean as fast as he could as well as get away from Ava. Her touch was burning him.

As soon as Cas set foot on the docks, he called out Dean’s name, and saw the man turn. Dean immediately started walking towards them with a smile on his face.

“Cas,” he said happily. His smile faltered when he saw Cas’s state of undress and worry settled into his features.

“Ava!” Cas warned, jerking his hand back to make Ava stop. “Let me go now.” He felt something sharp press into his side.

“Dean Winchester,” Ava announced. Dean hadn't noticed her until that moment. He looked over at her and his face immediately contorted into a look of hatred and anger. “I want to come on the Impala. I want to join your crew.”

“Let go of him,” Dean said, his voice deep and clear. His eyes flicked down to her other hand and something akin to absolute fury washed over his features. “Now. And get out of here. I’m not taking you into my crew.”

Ava’s grip tightened on Cas’s wrist sharply, making him yelp. “I’d urge you to reconsider.”

“Dean,” Cas pleaded. “Just let her join; if you don’t she’s going to tell everyone about us and you’ll never be able to come back to Heaven.”

Dean’s posture tensed and he took a step towards them, never taking his eyes off Ava, “Who do you think you're talking to?” he said.

“I’m sick of it here,” Ava said, ignoring Dean’s question. She jerked Cas forward. “If I have to hurt your little pet to get out of this town, you bet your ass I’m gonna do it.”

Dean’s eyes flared before he flicked them to Cas. “C’mon,” he said. “We shouldn’t talk about this here.” Dean pivoted and walked swiftly towards his ship. Ava started following him almost immediately. Cas chanced a look at her profile and saw a smile tugging at the corners of her lips.

Ava watched as Dean walked up the bridge onto his ship with wide eyes, not even bothering to use the ropes to help him to not fall. Dean disappeared over the edge as Ava hesitated. Cas turned to her. “Are you having second thoughts?”

“Shut up,” She hissed, spinning Cas so his back was against her side and she had a firm grip on him. “You better not fall,” she said and grabbed onto one of the ropes and climbed up onto the ship. They stumbled, almost falling over the edge. The knife Ava had jabbed into him, cutting through his clothes and the tip stabbed into him.

“So,” Dean said immediately, not missing a beat. His eyes were glued onto the knife in Ava’s hand. His features hardened as he saw blood stain Cas’s coat. “What is it you that you wanted?”

Ava straightened herself out. “I want to join your crew.” Laughs from the members of the Impala sounded on the deck. Ava gripped onto Cas’s wrist harder and pushed the knife into his side an inch more, drawing even more blood and a muffled yelp from Cas. “You don’t want to know what I’ll do if you don’t take me.”

Dean’s eyes flashed with rage and he began to say something but Jo came up and whispered something into his ear. He forced a smile onto his face before looking back to Ava, “Okay. You can come with us. I have a place set for someone just like you, actually.”

Ava narrowed her eyes. “What is that supposed to mean?”

“Ruthless, bold, selfish, angry, et cetera,” Jo announced. “That makes for a rounded pirate. We’ve been needing a new mate in the brig. Garth needs a buddy down there…” Jo trailed off. Cas could hear snickers and laughs, covered up with coughs, sound from the pirates on deck.

“Are you being serious?” Ava asked, her grip on Cas’s wrist loosening by the second. Cas shot Dean a look that hoped came across as him saying, ‘ _keep her talking_.’

“Absolutely,” Dean nodded. Cas heard the sarcasm carefully hidden in his words.

“What would I be doing with Garth in the brig?” Ava asked. Cas made eye contact with Dean for a second before yanking his wrist from her grip. She dropped the knife in her surprise, yelling and grabbing out at Cas as he sprinted into Dean’s arms.

“Cas!” Dean yelled, enveloping the boy in his arms and holding him tight. “I got you, baby, I got you!” Cas buried his face in Dean’s chest and clutched onto the pirate. “I got you.”

“Don’t let me go,” Cas whispered, on the brink of crying.

“Never,” Dean whispered back, fisting Cas’s shirt in his hands tightly.

“You bastards!” Ava yelled. Cas pushed his face further into Dean’s chest and inhaled, his resolve almost breaking at being able to be this close to his love again. “Let me go!”

“You didn’t let Cas go,” Jo countered, a laugh in her voice. “Alright mates, put her in the brig with Garth. He’ll finally have a _prisoner_ to talk to death, now.” Cas heard Ava yell as she was taken under deck.

“I missed you,” Dean whispered, turning his head to kiss Cas. “I missed you so much.”

“I missed you, too,” Cas responded, snaking his arms around Dean’s neck and fisting his hands in Dean’s coat to pull himself closer. “I’m so glad you’re back.”

“Me, too,” Dean said. He slid his hands to the back of Cas’s thighs and hoisted him up, carrying him to his cabin swiftly and laying him down on his bed gingerly — like Cas was a priceless piece of art.

They didn’t talk while Dean settled himself between Cas’s legs, busying himself with checking out the cut Ava had given him when he had settled in his normal spot.

“It’s not too bad,” Dean mumbled, reaching into his nightstand and grabbing gauze and a strip of cloth. He dressed it quickly, and Cas didn't have the want to tell him that he'd be able to heal himself by tomorrow morning. So he stayed quiet, and continued to lay in silence. Taking time to just feel the warmth of one another.

Cas felt his wrist healing and he breathed into Dean’s neck quietly, “My pirate…”

Dean shifted and Cas felt the man’s weight press into him pleasantly before he spoke in a soft voice. “Did she… Did she do anything to you? You’re not wearing much... Are you okay?”

Cas nodded and turned his head to the side, “Yeah.” He captured Dean’s lips with his and moaned quietly at the fact that he _could_ kiss the pirate again. Dean smiled against Cas’s lips and grabbed onto his hips. “I’m okay,” Cas said. “'The only thing she did was hide in my room and watch me undress.”

Dean clenched his jaw for a second before Cas ran a hand down his back to soothe him. Once he untensed, Dean rested his forehead against Cas’s and he swallowed to clear his throat. “Who even is she?” He asked.

Cas laced his fingers into Dean’s hair, tugging just slightly. “She was just a cook from my father’s staff. A while after you left, she came and told me that she knew about us and threatened to tell.”

Dean sighed, “I’m so sorry. I should’ve come back sooner.”

Cas shook his head, “Shut up,” he whispered. “And kiss me.” Dean’s lips were on his in a second and his tongue licking into his mouth.

Tugging Dean closer by his hair, Cas moaned as he felt Dean’s tongue trace along his teeth before tangling with his. Dean slid his hand down Cas’s body and palmed the boy’s groin with his hand, groaning as his hand made contact with the hardening member under Cas’s thin blue shorts.

Cas threw his head back, moaning Dean’s name and pushing his hips into Dean’s touches. Dean moved his hand out of the way and used his own hips to meet Cas’s. Both of his hands slid up Cas’s torso and interlocked their fingers.  

“Cas,” Dean moaned, placing sloppy and wet open mouthed kisses all along the soft skin of Cas’s neck. Cas inhaled quickly as his hips jerked of their own accord into Dean’s with no real coordination. He panted and gripped onto Dean’s hands tightly.

Cas started gasping out _‘yeah’_ and _‘yes’_ as his voice got higher in pitch with each word. Dean smiled and bit down where Cas’s shoulder and neck met lightly.

“Dean!” Cas whined, arching his back, “I’m so close!”

“You are?” Dean pushed his hips into Cas’s in a long, slow drag that had the boy gasping for breath and his thighs quivering.

“Just like that,” Cas panted out, wrapping his legs around Dean and digging his heels into the back of Dean’s thighs. “Dean... I’m gonna come!” Cas’s legs squeezed around Dean and his fingernails dug into the back of the pirate’s hands. “I’m gonna come!”

“Don’t tell me,” Dean said, grinding down into Cas. “Show me.” He sucked on Cas’s neck and made sure to rub against the boy in just the right way.

“Dean!” Cas screamed, bucking his hips wildly and roughly into Dean’s. Cas shook his hands out of Dean’s and wrapped them around the man’s neck, clinging to him tightly.

“Cas,” Dean groaned. He lifted his head from Cas’s neck and put his forehead against Cas’s, feeling himself come undone just as fast as Cas was. “Been so long,” Dean groaned. “I’m close.”

“Dean,” Cas gasped in a moment of clarity, making the older man lift his head and look into Cas’s eyes. The boy’s mouth dropped open and his eyelids drooped. Cas moaned Dean’s name loudly as he came again, pulling Dean with him in a erratic — almost painful — jerk.

Dean crushed his lips onto Cas’s and slid his tongue into the boy’s mouth to tangle their tongues together again. They both moaned and panted into each other’s mouths as their hips moved together, slowing down at a steady pace.

Cas kicked Dean’s legs out from under him to feel the man’s weight on him as they stopped their hips and pulled their tongues out of the other’s mouth. They rested their foreheads together, their heated breaths mixing as they panted.

“I missed you,” Dean breathed hard, “Missed you so much.” He pressed a chaste kiss to Cas’s lips, nibbling on his bottom lip before pulling away.

“I love you,” Cas said, threading a hand into Dean’s hair and pushing his head back down to connect their lips in a kiss that was more breathing than kissing.

“I love you, too,” Dean said, grabbing onto Cas’s hip with one hand while the other came and slid their fingers together. They kissed one last time before Dean settled his head over Cas’s heart and closed his eyes.

Cas’s heart slowed as he started falling asleep, only to pick up for one moment as he spoke. “Dean,” he whispered, “Never let me go.”

Dean smiled, squeezing Cas’s hand, “I’ll won’t let you go for as long as you want,” he said, “Don’t you ever let me go.”

Cas sighed happily, “Never...”

“...Ever.” Dean heard Cas’s heart even out and fell asleep listening to it.

~  ~  ~

_March 9, 1694_

 

Cas shifted uncomfortably. He could feel the sticky and unpleasant outcome of last nights activities still sitting in his drawers. “Dean, wake up,” Cas nudged the pirate. “Dean.”

Dean groaned and stretched before lifting his head and smiling at Cas. “Morning, sunshine,” he said, his smile fading and grimacing.

“It’s hardly morning,” Cas groaned. “It’s two A.M.”

Dean looked at the clock, “You have a point there,” he said, wincing more at the mess in his drawers before rolling off Cas and standing up.

“We didn’t clean up last night,” Cas said, still grimacing. He sat up on the bed and saw Dean cringe with him at the unpleasant feeling that accompanied his movements.

“No,” he said slowly, “It seems we didn’t.”

“What now?” Cas asked.

Dean chuckled and unbuttoned his trousers. “Here,” he said, sliding them and his drawers off his hips. He kicked them the rest of the way off as he pulled his shirt over his head, as well. Cas felt himself become flustered. “Give me your drawers and I’ll have them washed.”

Cas raked his eyes down Dean’s body, his breathing becoming uneven. He pushed himself up and off the bed, trying to hide the fact he was becoming aroused. “O-okay,” he stuttered, thumbing the hem of his own underwear — taking a moment to realize that if he took his underwear off Dean would know he was aroused — before pushing them off his hips. He stepped out of them, blushing as he bent down and picked them up to hand to Dean.

Dean put their clothes into his hamper and then came back over, sliding his hands around Cas and holding him close. Cas could feel himself blush as his skin was pressed flush against Dean’s. Dean chuckled softly. “Are you embarrassed?” He asked, kissing Cas’s forehead.

“I’m not embarrassed,” Cas answered, pushing his face into Dean’s neck. “I’m just… I… I’m still new to being this bare in front of another person. You and my nursery maid are the only people who’ve seen me naked.”

The pirate smiled fondly, chuckling softly again. “You don’t need to be shy around me,” Dean said, his smile turning into a smirk. “How about we get cleaned up now? I’m thinking… shower?”

Cas giggled. “Okay.” He wrapped his arms around Dean’s neck as the pirate lifted him up and carried them into his bathroom. “We won’t be doing much showering, will we?”

“Observant,” Dean said jokingly, “Aren’t you?”

“Of course,” Cas teased. Dean smiled as they entered his bathroom. He pushed Cas up against the wall opposite the shower and kissed him roughly. Cas opened his mouth when he felt Dean lick along his bottom lip and moaned as the man’s tongue pushed into his mouth and rubbed against his own. Dean’s hand left Cas’s thigh and snaked between them to take the boy’s cock in his hand. He ran his thumb over the tip of Cas’s length and felt the boy shudder and gasp.

Dean sucked a hickey into Cas’s neck before setting him down and reaching to turn on the water. Cas followed him, wrapping his arms around Dean’s torso and kissing over his shoulders and back as the water warmed up. Dean rolled his neck in appreciation and turned around in Cas’s arms, pulling him into the shower in the blink of an eye.

“Let’s get cleaned up, quick, then?” Dean smiled.

“Quick,” Cas agreed. Dean reached behind him and grabbed the soap. He got it wet and then started massaging his soapy hands over Cas’s body.

Dean leaned down to kiss Cas as the water washed away the soap suds. Cas tangled one of his hands in Dean’s hair as the other one trailed down his arm and grabbed the bar of soap. He pushed Dean’s back against the tiles and smiled as Dean hissed at the coldness.

Cas soaped up his hands and raked his eyes over Dean’s front as his hands left trails of soap where they went.

Dean chuckled, “Admiring the view?” He asked, putting his hands on his hips. “I thought you wanted to get to the good part?” Cas gave him a mischievous smile.

“I have gotten to the good part,” He said, reaching down and taking Dean’s manhood in his hand. Dean inhaled as Cas started moving his hand along his length slowly, sliding easily due to the soap. Cas leaned forward and nipped at the man’s neck, speeding his hand up. Dean groaned and let his head fall back. Cas sucked small hickeys all over Dean’s neck as he pumped his hand.

“Seems to me,” Dean said, his words coming out airy. “That it’s only you that has gotten to the good part.”

“Nothing’s stopping you,” Cas mumbled. The next moment had Dean spinning them around and pushing Cas’s arms above his head.

“How would you like it?” Dean asked, taking both of the boy’s wrists in one hand and letting the other come to splay over Cas’s stomach. “'How do you want me to fuck you?”

“Hard,” Cas said, forcing himself not to blush. “Fast. I want to be able to feel it for hours after.”

Dean inhaled slowly. “Whatever you want, angel, it’s yours,” he said, letting go of Cas’s wrists before he spun him around and pulled the boy’s back into his chest.

“You want it fast and hard?” Dean asked, smoothing one of his hands over Cas’s chest and stomach — making sure to give extra attention to his nipples — while letting the other come to take the boy’s cock in his hand.

“Yeah,” Cas said, closing his eyes and moaning as he felt Dean’s hand pump over his shaft. “And Rough.”

“Hard, fast, _and_ rough?” Dean asked, quickening his hand. “You’ve got to be the most spoiled boy in all of creation.”

Cas let his head fall back against Dean’s shoulder, moaning breathily. “It’s your f-fault.”

Dean laughed, “I guess it is.”

“Faster,” Cas gasped, turning his head into Dean’s neck. He panted out the pirate’s name as his hand on his cock got faster and the one playing with his nipples got rougher. “Dean, I want you inside me.”

“So, _so_ spoiled,” Dean mumbled. He pushed Cas’s chest into the cold tiles roughly before moving his hand up to Cas’s mouth. “Suck,” he ordered. Cas enthusiastically swirled his tongue around the digits, moaning around them as Dean’s other hand came back to play with his nipples.

“Dean, please,” Cas moaned around the pirate’s fingers, pushing back to feel Dean’s hard member. Dean removed his fingers from Cas’s mouth. “Oh, fuck Dean, please? I need you now.”

“Calm down,” Dean whispered, moving his fingers to circle Cas’s rim and making the boy cry out and push back against him.

Cas whimpered brokenly as Dean pushed his finger into him. He moaned and tried to fuck himself back on Dean’s fingers. “Oh god, I love you,” he gasped, “I can never make myself feel like you do.”

“Hm,” Dean hummed. “You finger yourself and think of me when I’m gone, angel?” he asked, adding another finger slowly, scissoring them to open Cas up.

“Yeah,” Cas gasped, moaning loudly.

“How often?” Dean asked, brushing past Cas’s prostate and making him jerk himself into Dean.

“Dean, please, I’m ready,” Cas begged, scratching at the wall desperately.

“How often?” Dean insisted.

“I don’t know,” Cas cried, his arm flying back to grab onto Dean’s forearm. “Every other night?”

“Hm,” Dean mumbled. He pulled his fingers out before pushing them back in roughly and curling them into Cas’s prostate.

“Dean!” Cas yelled, pushing his hips back to meet the man’s hand. “Please!”

“None of the toys I gave you are as big as me, are they?” Dean asked.

“Nothing is as big as you,” Cas whimpered out, “Please?” He turned his face to look at Dean over his shoulder. Smirking, Dean pushed Cas flush against the tiles.

“Nothing’s as big as me?” Dean confirmed, “That must drive you crazy.”

“Yes,” Cas gasped. He felt the coldness of the tiles against the tip of his heated cock. “God, Dean, _please.”_ Cas heard Dean chuckle before the man pulled his hips away from the wall. Dean’s hand came to rest on his upper back, keeping him still.

“Don’t move,” Dean said, leaning away from Cas to grab a bottle of oil.

“You keep oil in here?” Cas asked breathlessly.

“Believe it or not, but sometimes I miss you when I’m gone, too,” Dean said, smiling and facing away from the stream of water to oil his cock up. “And it’s easier to use oil than water as a lubricant.”

Cas giggled, “Dean The Righteous Man Winchester, The Pirate King, the most feared man to sail the seas, masturbates in the shower?”

Dean smiled as he guided the head of his cock to Cas’s hole. “You betcha,” he said, thrusting in quickly and setting a fast pace. Dean leaned forward to Cas’s ear. “And to the thought of you in front of me: on your knees and my dick in your mouth.”

“Really?” Cas asked, pushing back to meet Dean’s movements and gasping when his prostate was hit. “Maybe I can — ah! — can fulfill that daydream — ah!”

Dean groaned and grabbed onto Cas’s hips. “You want it rough?”

“Yes,” Cas pleaded. Dean thrusted into him and Cas keened, “Harder!”

“Harder?” Dean panted, “Whatever my angel wants.” He dug his fingers into Cas’s hips and pulled him back onto his length as he thrust forward.

“Yes!” Cas screamed, “Just like that!” Dean’s thrusts got quicker and harder with each passing minute. Cas felt his legs begin to tremble from both the pleasure and keeping himself up.

“Don’t worry, angel,” Dean said as pulled Cas back again and snapped his hips forward, causing Cas’s legs to give out. “I got you.” Dean held Cas up while still thrusting hips.

“Dean,” Cas whined, feeling heat start to pool in his abdomen. He gasped as he felt Dean pull out. “No!” Dean shushed him as he turned the boy around and hooked his arms under his knees.

“I wanna be facing you,” Dean said, thrusting back into Cas.

“Oh!” Cas threw his head back and gripped onto Dean’s hair and tried to pull the man’s head towards his neck. He cried out when instead of sucking hickeys into his neck, Dean craned his head down to take one of his nipples into his mouth. “Dean!”

Just for a second, Dean’s lips weren’t on his skin as he spoke. “C’mon,” he husked. “You can come.”

“No,” Cas whimpered. “Want you to come.”

Dean smirked, biting down roughly on Cas’s sensitive nipple. “Come,” He growled, thrusting harder and faster and angling his hips to hit Cas’s prostate.

Cas screamed, _“_ _Dean_ _!”_ He held onto Dean for everything he was worth and came so hard he wasn’t able to move.  

“Fuck,” Dean groaned and followed in his release, looking up at Cas’s face as he did. He thrust once more, almost collapsing at the whimpered moan that came out of Cas: completely wrecked and blissed out. “I love you…” Dean breathed. Cas panted, trying to catch his breath enough to respond. Of course, he didn’t need to. But he wanted to, and Dean gave him the time he needed to be able to recover.

“Love you,” Cas breathed out. “Love you, too.” They stayed like that until Cas started shivering from the water turning cold. Dean cleaned the cum from between them before reaching over to turn the water off.

“Let’s get dressed and we can lay together for a bit to get you warm again,” Dean said, helping the boy onto his feet. Cas nodded and held onto Dean as he led them out to his bedroom, again. He dried them both off before searching around for clothes and when he found two suitable outfits, Dean dressed and then started on Cas.

“I’m still cold,” Cas complained, trying to pull Dean up from lifting each of his feet to slide into a fresh pair of drawers and trousers. Cas wanted to snuggle into him to get warm.

“Cas, hold on, I need to get you dressed,” Dean said, “Stay still.”

“But I’m cold and you’re warm,” Cas protested. Dean batted his hands away and stood up, pulling the articles of clothing with him to rest on Cas’s hips.

“If you stay still, then I can finish faster and we can get under the covers of our bed again,” Dean tried to reason with a tired, cold, and cranky Cas.

“But that will take forever! I want to be warm now,” Cas pouted. Dean sighed as the boy tried to burrow into his side while he grabbed a shirt for Cas.

“It won’t take forever if you cooperate,” Dean tried again.

“Dean,” Cas whined.

“Cas,” Dean said right back, “Now arms up.” Cas huffed and lifted his arms to let Dean slide the shirt on. Dean situated the shirt and then swept Cas off his feet. “See? That didn’t take so long.”

Cas smiled happily, “Bed,” he whispered, snuggling into Dean farther. “It took longer than I wanted.”

Dean chuckled, sliding into their bed and pulling the covers up around them. “If you had stayed still, like I asked, it wouldn’t have even taken a minute.”

Cas yawned, “Still too long.”

“I love you,” Dean laughed, kissing the top of Cas’s head.

“Mh-hm,” Cas hummed. “I know.” He kissed Dean’s chin. “I love you, too.”

“I mean it, Cas,” Dean said. Cas opened his eyes and looked up into Dean’s.

“I know,” he said, smiling. “I mean it, too.” Cas kissed Dean lovingly.

“I don’t like leaving you,” Dean whispered, hugging Cas tightly. “It tears me up inside. I hate it, Cas. I hate leaving you alone for such long periods of time.”

Cas scooted up on the bed to be eye level with Dean. “You don’t leave me,” he said softly, cupping Dean’s cheek with one hand and running the other through his hair. “Well, maybe physically. But you never have left me. Not really, anyway. You’re always with me,” Cas whispered. He took Dean’s hand and placed it over his heart. “In here. I know I’m not alone.”

Dean looked into Cas’s eyes, not searching for anything. Just… Looking. “After all I’ve done… I don’t deserve you, but you give me your love anyway. You are truly my angel.”

“You deserve happiness,” Cas whispered, “You deserve to get what you want.”

“Well,” Dean said, “I want you.”

“I have news for you, Winchester,” Cas said, smiling. “You’ve already got me.”

“Forever?”

“For always.”

**Notes for the Chapter:**

> I'm going to be posting the next chapter next week (July 8th) at about 2 pm. Thank you for reading! Let me know how you like it and drop by my tumblr if you want! 
> 
> https://bttmcas-confessions.tumblr.com


	12. Chapter Twelve

**Notes for the Chapter:**

> Hey guys! I'm so sorry I didn't get this up yesterday. I got grounded... Which I think is ridiculous because I'm over 18 and there is no reason for her to ground me and I did all my chores and even half of my brothers................ But whatever. 
> 
> I hope you like this chapter! I don't feel like I did too good. But let me know?

Chapter Twelve

_March 9, 1694_

 

Dean paced in front of her cell. Ava sat on the wooden bed frame, watching him with angry eyes.

“She hasn’t said much,” Garth spoke up, his voice happy despite where they were. “It’s been great actually. I love having someone to talk to.”

“I bet,” Dean said, smiling at Ava dangerously. “Can you give me a moment alone with her?”

“You bet,” Garth replied, standing up and almost skipping out of the brig.

“Well,” Dean said, once the door closed behind Garth. “Ava.”

“You better let me go, or so help me I’ll—”

Dean cut the girl off with an incredulous and harsh laugh. “You’ll what?” He asked, “You’ll kill me? You’ll tell everyone about Cas and I?” Dean laughed again before seeing red and looking her straight in the eyes. “You won’t be telling anyone about Cas and I.”

Ava visibly shrunk away from the pirate’s gaze. “I swear I’ll do it. As soon as you let me go—”

“Let you _go?_ Are you _joking?_ You think you’re getting out of here? How cute,” Dean said, faking sympathy. “I’m not letting you anywhere near Heaven — or Cas, for that matter. As soon as we take off again, I’m sailing you to an island way out of the way of civilization and dropping your sorry ass there. You won’t be seeing another human for as long as you live.”

Ava’s eyes widened. “You… You can’t do that.”

“Watch me,” Dean said, calm, cool, and venomously. “You threatened someone I love. I don’t take kindly to that.”

“Cas—”

“ _You_ don’t get to speak _his_ name!” Dean shouted, storming over to rattle the door to Ava’s cell. It clanged loudly and made the girl cry out in fear. “You don’t get _anything_.”

“I-if you let me go I won’t say anything,” Ava pleaded. “I swear.”

Dean raised his eyebrows incredulously and spoke. “Really?” he asked, unable to comprehend who this girl thought she was. “You want to try _that?”_ Ava’s face crumpled. “After what you did to _my_ Cas?... I don’t fucking think so, sister. You _threatened_ him — threatened the man _I_ love. And you think you can just try and apologize?” Dean scoffed. “Not gonna fly. Not with me, not with Cas, not with anyone on this ship. You’re _stuck_ here.” Ava cowered as Dean spoke. “You threatened _me_ by threatening Cas. Do you know what I do when I feel threatened?”

“No,” Ava whimpered, hugging her knees to her chest. Dean bared his teeth in an animalistic smile.

“I make Hell seem like a drink of water on a hot day,” he said, keeping his voice low and dangerous. “I make the Gods _weep_ for the fools that dare cross me. I make the waters of the heavens run red with _blood_. I fight. And I don’t just kill. I torment and I martyrize.”

“You’re going to kill me?” She squeaked.

Dean looked at the ground and shook his head, “No, no, no. That’d be too easy.” He looked back up into her frightened eyes. “I’m going to make you _suffer_ .” Dean paused, watching her cower even further away from the cell door. “You’re talking to Dean _The Righteous Man_ Winchester. I’m the Pirate King… And you just held the one I love at knife-point. You just took the one thing I care for most in this world, and threatened him. You threatened _me_.

“Let me just ask you this: how _stupid_ are you? You’ve heard the rumors; you know the kind of man I am. So what in the world makes you think that you’d get away with _that?”_ Ava didn’t answer. She sat on the bed frame and tried to make herself as small as possible. Dean shook his head in disbelief before turning and walking away from her cell. “Bye, Ava. Have fun with Garth for the next few weeks. It’ll be some of the last human interaction you have for a long, long, long, _long_ time. So long you’re going to wish the only thing I had done to you was kill you.” He slammed the door behind him, yelling to Garth he was done.

Jo was waiting for him when he got to the main deck. “How’d it go?” She asked, walking beside him cautiously.

 _“I’m fucking pissed,”_ Dean said. He stopped and looked around, trying to find something to take his mind off Ava and what she did to Cas. “I’m _beyond_ pissed. She threatened Cas. Who the fuck does she think she is!? Using Cas as leverage!? She’s gonna pay. _Fuck!_ I’m gonna — I’m gonna… _Fuck!”_

“Dean,” Jo said, slowly coming over to put her and on Dean’s shoulder.

“Don’t touch me,” Dean said harshly, shrugging her hand off. “Don’t touch me right now.”

Jo backed away and put her hands up. “Okay, Dean. I’m not going to touch you.” Dean kept his eyes on her. “I won’t touch you,” She said, again. “But I’m gonna talk with you.”

Dean took a moment to breathe. “Fine.”

“Listen to my voice, okay?” She said, “Are you listening?” Dean nodded. “What Ava did was bad, but everything is okay now.”

“Not likely,” Dean scoffed. “She made Cas worry for months. That does something to a person.”

“Is Cas dead or dying?”

“No.”

“Are you dead or dying?”

“No.”

“And Ava is going to pay,” Jo said. “Everything is fine. Cas doesn’t have to worry anymore. He’s okay, you’ve taken that weight off his shoulders.”

Dean sighed, “You’re right. But I’m still pissed, Jo. She… She…”

“She did something horrible and now she’s going to pay. You need to leave it at that.”

“You’re right again.” Dean sighed and ran his hands over his face. Jo came over and took his hand in hers, staying quiet and looking out over the water.

“Why don’t we start getting some inventory done?” She asked.

“Of course,” Dean responded, giving her hand a squeeze. “Just give me a couple of minutes.”

“Alright,” She said, letting go of Dean’s hand. “I’ll get the swabs a warning to get ready to work.”

~  ~  ~

_March 29, 1694_

 

Dean had decided to stay a little longer than a few weeks this time. Something in which Cas was thankful for. He’s already admitted it to Dean, but Ava had really messed with him. Not in any way that was permanent. But she’d gotten so close to telling everyone their secret, and Cas couldn’t stand to think about what he would do without being able to simply just hold Dean.

When Cas asked what Dean was going to do with Ava, because he couldn’t just let her out and back into Heaven obviously, Dean told him he had it taken care of. Cas realized it was probably something that wasn’t exactly legal and/or moral and he didn’t push Dean for an answer. He trusted Dean’s words and let the debacle fizzle out.

At the moment, Dean was singing him to sleep. Cas wasn’t really listening to the words, he just liked putting his head to Dean’s chest and feeling the rumble as he sung.

“Shit!” Dean suddenly gasped. Cas startled to full alertness and sat up, staring at Dean with wide eyes. “I missed your birthday. Damn! I had something for you, too.”

Cas laughed and shook his head. “It’s fine, I don’t really care. I’m not an avid birthday celebrator, either.”

“But… Your birthday…” Dean mumbled. Cas smiled and crawled on top of Dean, placing his head into the crook of Dean’s neck.

“It’s okay,” Cas shushed him. “You’re the only gift I need.”

Dean smiled, wrapping his arms around Cas’s smaller body and kissed his forehead. “I love you.”

“I love you, too,” Cas responded. “But I’m mad at you.”

“What? Why?”

“You made me wake up when I was almost asleep,” Cas said, yawning.

“Oh, you poor thing,” Dean laughed, “Your life must be so hard.” Cas smiled, kissing Dean’s neck.

“It is,” He joked. “Thank you for empathizing with my pain.”

“Of course,” Dean said, laughing softly into Cas’s hair. “Do you want me to keep singing?”

Cas sighed, “Yeah.”

“Okay,” Dean pecked the top of Cas’s head. “I’ll do anything for you.” He started humming the tune of a pirate’s song before softly singing the words. Cas traced his finger over Dean’s heart in random squiggles to the words Dean was singing.

Cas fell asleep listening to Dean and with a smile on his face. Dean’s voice was beautiful. He couldn’t hit all the notes he wanted it, but it didn’t matter. Not to Cas. To Cas, that made Dean’s voice even better. It made Dean as a person even better.

~  ~  ~

Dean woke Cas up late in the night by kicking his legs out and thrashing his head against his side.

“Dean,” Cas whispered, shaking the man’s shoulder. “Dean, hey, wake up. You’re having a nightmare.”

“Stop!” Dean yelled. “Let me go!”

“Dean,” Cas tried again, shaking him harder.

“Alastair, please _stop!_ Please! I don’t want this! _Stop_ !” Dean screamed and sat straight up in bed, clutching the sheets, sweating, and breathing hard. “ _Don’t_ touch _me!”_

Cas gave Dean a moment before speaking. “Dean?” he asked, scooting down on the bed to see Dean’s face.

“I’m awake,” he said, his voice cracking. “I’m _awake.”_

“You are awake,” Cas whispered. “You had a nightmare.” He slowly reached his hand up to Dean’s face. “May I?”

“No,” Dean whispered. “Not yet.” Cas put his hand back down and waited for Dean to calm himself.

“What can I do?” Cas asked, keeping his voice low and soft. Dean squeezed his eyes shut.

“Just… Just stay there,” Dean said, his body shaking. Cas nodded, pushing into the mattress to make it dip and tilt Dean’s body. “Can you… Can you talk to me?”

“Of course,” Cas said, “What would you like to talk about?”

“Anything,” Dean said. Cas thought for a moment before he began.

“Did you know that bees never sleep? And that there are three types of honey bees: the queen, the workers, and the drones,” Cas said, seeing Dean smile a little bit. “Honey bees fly at 15 miles per hour and their wings stroke 11,400 times per minute, thus making their distinctive buzz. And they’re the only insect that produce food for humans. They will usually travel approximately 3 miles from their hive. They’re the only bees that die after they sting, they have five eyes: 3 small ones on top of the head and two big ones in front. They also have hair _on_ their eyes! That’s just weird. It’s got to be rather uncomfortable, too… And did you know, bees communicate with each other by dancing and by using pheromones.”

“Really?” Dean asked, looking up and meeting Cas’s eyes. Cas nodded.

“Some interesting bee facts for you,” he said, smiling wide. Dean smiled back and took a deep breath.

“Okay,” he said quietly. “I’m okay.”

“Are you sure? I’ve got more bee facts I can tell you,” Cas asked, bringing his hand up slowly. “May I?”

“Yeah,” Dean nodded. Cas cupped his face and felt Dean lean into his hand.

“Are you sure you’re okay?” Cas asked. “We don’t need to rush.” Dean let out a deep sigh that he didn’t really know he had in him.

“Yeah, I’m okay.”

“Do you want to talk about it?” Cas asked, scooting closer and sliding his hand from Dean’s face to settle over his heart.

“Y-yeah,” Dean stuttered. He didn’t sound convincing, though.

“You don’t have to, Dean,” Cas whispered. He pushed Dean back down and snuggled back into his side. “We can go back to sleep.”

“No,” Dean answered almost immediately.

“Okay,” Cas said, sliding his fingers between Dean’s for comfort. He moved up the bed to be eye level with Dean and Dean turned onto his side to be face to face with Cas. “Let’s talk, then?”

“Okay,” Dean whispered, looking into Cas’s eyes.

“How did the dream start?” Cas asked, squeezing Dean’s hand for support.

“It wasn’t… It wasn’t a dream,” Dean said. “It was a memory.” His eyes started to redden and he started to sit back up.

“I got you,” Cas said, throwing his leg over Dean’s and pulling them closer together. “I have you, Dean, you’re here in my arms. Okay?”

Dean shut his eyes and nodded. “Yeah,” he whispered, opening his eyes back up and looking to Cas’s. “Okay.”

“Are you alright to describe it to me?” Cas asked. He had been preparing himself for this so he could help Dean as best he could. Cas was ready to hear about the torture Dean had to go through when he was with Alastair.

Dean nodded. “Yeah…” He still didn’t sound convincing.

“It’s okay, Dean,” Cas said, giving Dean a reassuring smile. “It’s okay if you’re not able to share. You don’t need to force yourself to do something you’re not ready for.”

“But I do,” Dean whispered. Cas brought his unoccupied hand up to Dean’s hair and ran it through, just the way he knew Dean liked. “I do. I want to. I want to tell you. I trust you.”

“Okay,” Cas agreed. “Take your time, Dean. You can take your time.”

“No. I’ve just got to get it out,” Dean said, taking a deep breath and locking his eyes onto Cas’s. “I don’t really know where to start… But…”

“What’s the first thing you remember?” Cas asked, keeping his eyes on Dean’s.

Dean swallowed. “I… I was in my cell,” he started. “It was my fourteenth birthday again and he came and took me. He had me taken to the usual room, b-but I was cuffed to a wall instead of the table. And then my clothes — rags, would be more accurate — were ripped off so I was naked for him. Alastair… touched me. He touched me where he’d never touched me before because I wasn’t supposed to feel pleasure — I didn’t want to. I was only supposed to be for him to use to get _his_ pleasure… But he knew what he was doing to me. And I didn’t want to, Cas, you have to believe me; I didn’t want to enjoy it — I tried to hard to get him to stop _touching_ me there. I fought so hard to get his disgusting hands off me but I… I couldn’t — he wouldn’t stop!”

“It’s okay, Dean,” Cas whispered, using his thumb to wipe away the tears that had began to fall from Dean’s eyes.

“No, it’s not!” Dean cried. “He got me to come _over and over_ again. You have no idea how fucked up it makes you to get off to something you don’t want to enjoy.” Dean tried to hide his face in Cas’s neck, but Cas stopped him. He screwed his eyes shut and locked his jaw.

“Hey… Dean,” Cas said softly, waiting for Dean to look into his eyes again.

“He just kept _touching_ me and forcing me to—” Dean cut himself off with a gut-wrenching sob. “H-he made me think that deep down I wanted him to touch me. He almost brainwashed me into thinking I liked when he raped me.” Cas let Dean hide his face now. “He did it so many times on just that day. I was so fucking exhausted. I just wanted to die, Cas. I wanted to never have been born…” Dean cried harder.

“I got you,” Cas soothed, pulling Dean into him and rolling onto his back with Dean on top of him.

“I thought… I started to think that I wanted him to do those things to me. I thought because I had orgasms, that I must be enjoying it. It was so fucked up. It fucked me up so much, Cas.”

Cas stayed quiet and let Dean cry into his neck. He closed his eyes and cradled Dean’s body into his for what felt like hours before he finally spoke. “I’m so sorry. I’m so sorry he did that to you. You don’t deserve that… You deserve so much _better_ than that.”

“Do I, though, Cas?” Dean asked, pushing himself up. _“Why?_ I’m not special. I’m not a good person. I torture and hurt and I _kill_ people for a living. How in the world do I deserve more than the absolute worst? _How_ do I deserve better than complete hell?”

“Don’t talk like that,” Cas chided. “You know you’re not a bad person.” He sat up, trying to pull Dean back down with him, but Dean shook his head. Dean moved away and sat on the edge of the bed, hanging his head in his hands. “Dean—”

“Gods, Cas! You don’t understand! I torture people! I torture them and make them wish they were dead! That’s just like how Alastair made me feel. I didn’t take what happened to me and turn myself into a better man! I became a different version of Alastair.”

“Dean,” Cas started again. “I’m afraid—”

“You should be afraid of me!” Dean yelled. He refused to look at Cas. “You should be afraid of me… The things I do when I carry out my deals… You have no idea how merciless I am.”

“I’m not afraid of _you,”_ Cas whispered. Dean froze and looked at him with confused eyes.

“What?” He asked, taken aback.

“I’m not afraid _of_ you,” Cas repeated, louder. “I’m afraid _for_ you. I’m afraid for you because I think you’re too scared to _be_ scared in front of anyone... Even me.” He came behind Dean and sat on his knees to hug Dean, resting his chin on Dean’s shoulder. “I _understand_ . I know the past is scary to relive... And I know it hurts. But the only way to heal the pain is _through_ it. You’re in a box of not accepting that you _are_ scared. You have to accept that you’re scared. You have to accept that you’re scared of feeling that pain — of reliving it. I know its easier to just give up, and tell yourself that hell is better than whatever it is that’s happening right now, but it’s not… Dean…

“And I guess I did lie to you about being afraid of you. But I’m not afraid of you because of the reasons you think. I’m afraid of you because I’m so afraid _for_ you. I don’t want you to feel hopeless or that you’re alone a-and I don’t want to lose you… It’s not okay what Alastair did, you have to know that and you have to _accept_ that. Anyone who tells you differently is lying to you; Deep down even that monster knows what he did is wrong.”

“Stop.” Dean shrugged Cas off and walked a few steps away from their bed.

“So much _bad_ has been done to you that you don’t know how to deal with the _good_ … You’re so used to bad things happening, but good things do happen, Dean Winchester.”

“Not in my experience,” Dean said, shaking his head.

“You don’t think you deserve to be happy?” Cas asked, pausing to look at Dean for an answer. “That you don’t deserve to be saved? Even if it’s from yourself.” Dean he stayed silent and kept his back to Cas. “What about Ben? Or Lisa?” Cas continued, “Aren’t they good things that’ve happened to you?”

“Good things happen to good people and I am not a good person.”

“Well, you’re not a bad person,” Cas countered.

“Oh, well, if I’m not good or bad then what am I, Cas? _What am I?”_ Dean snapped angrily. Cas was taken aback by his words. He knew Dean wasn’t mad at him; Dean was hurting.

“You’re human,” Cas said. “You’re a human somewhere between good and bad. I happen to think you’re more good than bad. You’ve helped and saved so many people, Dean.”

“I’ve also hurt and killed so many people, Cas,” Dean said, turning around and sighing in annoyance. “You’re making me out to be some hero when I’m not.”

“But you are, Dean! You are a hero. You’ve gotten rid of some of the nastiest people on earth because of your Demon Deals.”

Dean scoffed, “There’s nobody that I can name that thinks that other than for selfish reasons.”

“Ben,” Cas started. “Lisa, Jo, Charlie, Gilda, Sam, Kevin, everyone on your ship… Me.” Dean’s eyes shot over to Cas’s. “ _You_ saved all of them! You saved _me.”_

“Saving a whole bunch of people doesn’t make up for the bad I’ve done,” Dean said. Cas saw Dean’s face change from a look of self-hatred and hurt to one of guilt and sorrow. Dean turned away from him again.

“Maybe,” Cas said, standing up and walking over and turning Dean back around. He slid his arms around Dean’s neck, tilting his head up to look into his emerald eyes. “But it definitely doesn’t make you a bad person. You’re good enough that I, the _‘walking definition of innocence’_ as well as a descendant of _literal_ angels, fell for you.”

Dean let out a shaky laugh, “We’ll agree to disagree about my goodness, then.”

“For now,” Cas closed his eyes and brought Dean down to kiss him. “For now we’ll agree to disagree.”

“What do you mean by that?” Dean asked, leaning into Cas involuntarily.

“For now, we agree to disagree. But in the future, I’m going to get you to see you’re not what you think you are. You’re so much more.”

Dean chuckled dryly. “Okay, Cas,” he said, “Whatever you say.”

“I’m serious, Dean,” Cas insisted. He looked into Dean’s beautiful green orbs. “I’m not joking.” Dean shifted between Cas’s eyes, searching for something — anything to help him understand why Cas was so adamant about this... He really didn’t need to search, though. The answer wasn’t something he needed to search for anymore. It was always present in Cas’s eyes when he looked into them. “I love you, Dean.”

“Okay,” he whispered. “I love you, too.”

“Are you okay to go back to bed or do you want to stay up?” Cas asked, moving his hands down to Dean’s chest.

“Stay up,” Dean answered. “I don’t want to go back to sleep.”

Cas smiled and fisted his hands in Dean’s shirt, tugging the man with him as he backed up to the bed. “Okay,” he said, pulling Dean on top of him once the back of his shins hit the comforter. Dean smiled and settled between the boy’s legs, stopping to intertwine their fingers. He leaned down and kissed Cas, the painful memory of Alastair fading away with each touch of his lips against Cas’s. He didn’t know how, but Cas had healing touches; and he was sure it _wasn’t_ from his Grace. It was something that was purely Cas and something he was certain only Cas could do.

“I love you, Dean,” Cas whispered, pulling him down into a heated kiss. “I love you enough for the both of us; and I’ll continue to love you until you learn to love yourself, too.”

Dean rested his forehead against Cas’s and smiled. “I’m so in love with you, Cas,” he said, feeling more tears come to his eyes and had to concentrate hard on not letting them fall.

“You don’t have to hide anything from me,” Cas whispered, rubbing his thumbs over Dean’s eyelids. “You don’t have to pretend.”

“I know,” Dean said, his voice breaking.

“You’re allowed to be vulnerable in front of me,” Cas said softly, cupping Dean’s face with both of his hands. Dean nodded and tilted his head down to kiss Cas again. He pulled back just for a second to remove his own shirt and then moved his hands under Cas’s shirt.

“Can I take this off?” Dean asked. He wanted to be able to feel his skin against Cas’s.

“Yeah,” Cas breathed out, lifting his arms for Dean to slide it over his head and throw it on the floor. Dean immediately put his hands back on Cas’s body, trying to touch every part of him at once.

“How did I get so lucky?” Dean mumbled, dragging his lips over any part of Cas’s skin that he could.

“I should be asking that question,” Cas said. He traced along the scars and lines of Dean’s body. “You’re so beautiful, Dean. Really, there isn’t a thing I would change about you.”

Dean smiled in thanks as he pushed Cas’s arms above his head and threaded their fingers together. It felt so amazing just to be able to _touch_. “I love you, Cas,” Dean said.

“I love you, too,” Cas responded, closing his eyes as Dean’s hands roamed over his body.

“I’m sorry I got so upset,” Dean whispered, leaning down and resting his cheek against Cas’s collar bone. “I’m so sorry.”

“You don’t have to apologize,” Cas responded, squeezing Dean’s hands.

“I just—”

“I understand,” Cas interrupted Dean, gently. “You don’t have to explain yourself to me.”

“Thank you,” Dean sighed. “Thank you, Cas.”

“I _love_ you, Dean Winchester,” Cas whispered. Dean took his hands out of Cas’s and smoothed them over the exposed skin of Cas’s torso.

“I love _you_ , Cas,” Dean whispered back. Cas’s hands came to run through his hair and scratch lightly down his back while Dean splayed his hands over Cas’s chest and stomach.

 _Touch…_ Tonight, touch was more than enough for both of them.

~  ~  ~

_April 6, 1694_

 

Saturdays were Dean and Cas’s favorite days of the week. Cas didn’t have schooling or town meetings and he was free to spend them however he liked. And seeing as Michael _did_ have town meetings or other duties he had to attend to, Cas could spend all day with Dean doing whatever they pleased.

“What would be a good way to say ‘I ganked this bitch so fast she didn’t barely had time to scream?” Dean asked, looking over at Cas on their bed, reading a book. He was lying stretched out width-wise on the bed on his back with the book held above him.

“How did you kill her?” Cas asked, setting his book down and rolling onto his stomach to look at Dean.

“I stabbed her in the lungs,” Dean replied smoothly. It used to feel odd to talk about his work with Cas, but the kid had a talent for professionalism and how to word sentences better. Plus he wasn’t even phased by Dean’s bluntness anymore.

Cas looked thoughtful for a second before smiling brightly and saying, “The target was silenced within a single breath.”

Dean smiled back at him, raising his eyebrows. “Ah,” he said, writing it down and laughing. “That’s good.”

Cas pretended to bow, “Thank you. I try.”

“Okay, go back to your book,” Dean chuckled.

“I’m bored.” Cas rolled back onto his back and let his head hang off the bed. “When are you going to be done?”

Dean smiled, looking over at him out of the corner of his eye. “Soon.”

“How soon is soon?” Cas asked, rolling his eyes.

“What do you want to do?” Dean asked, putting his papers down. Cas smiled and rolled onto his stomach once again.

“Nothing,” he giggled. “Maybe just talk, cuddle, kiss, and if that leads to other things… I wouldn’t be opposed.”

Dean looked at him with raised eyebrows. “Now who’s libido is unquenchable?”

“What are you talking about?” Cas asked, quirking an eyebrow.

“I made you come _four_ times last night,” Dean explained.

“Dean,” Cas drawled, as if he was being stupid. “That was last night. It’s two in the afternoon. That’s eight hours away from being a full day later.”

“Gods, you’re so cute,” Dean sighed. He picked his papers back up and laughed. “I’ll be done soon.”

“Well, if you take too long, maybe I’ll start without you,” Cas teased, laughing and picking his book back up.

“You wouldn’t dare,” Dean fake gasped.

Cas smirked at him and teasingly said, “Watch me.”

“I better hurry up then,” Dean clicked his tongue.

“You better,” Cas laughed, looking back down at his book as Dean went back to the paperwork for his Demon Deals. Dean was able to get some work done before Cas got bored again. The kid started shuffling around on the bed and making suggestive sounds that had Dean almost snapping his pen in half.

“You know,” Dean said, his voice coming out an octave higher than he wanted it to. “If you’d quit moaning over there I’d be able to get my work done faster.”

“But I’m bored _now_ ,” Cas complained. He propped his head up on his palms. “I want you to shove your tongue down my throat _now_.”

Dean looked at Cas and groaned, “Gods.”

Cas smirked happily. “Well, on a different topic, you are right about one thing.”

“Oh? And what’s that?”

“I do need more time before we make love again,” Cas said,  “But, I’m also right about one thing.”

“Just one thing?” Dean asked.

“Well, I’m right about ninety nine percent of the time but that’s besides the point.” Cas waved his hand dismissively.

“So that was the one time I was right?” Dean asked, an amused smile on his face.

“Wrong,” Cas said, “You can’t be right again because then I’d only be right ninety eight percent of the time.”

Dean laughed, sitting forward in his seat. “Okay, what were you right about?”

“We will fuck tonight,” Cas stated. Dean inhaled through his nose.

“Okay,” he said, watching Cas closely.

“And I’m gonna tease you until we do.”

“How are you going to do that?” Dean asked.

“By getting _vocal_ ,” Cas said, smirking. “I know you love how vocal I am.”

“I do,” Dean said, clearing his throat and sitting back in his chair. “I do love how vocal you get.”

“Mh-hm,” Cas nodded, “Tonight’s going to be fun.”

“For you,” Dean said, his voice just a little hoarse. He cleared his throat again.

Cas smiled again, “Okay,” he said. “You can get back to work now.”

“What?” Dean gaped. Cas ignored him and picked his book back up. Dean sighed and went back to work, unable to focus because Cas had started letting out little gasps and whines every now and then. “You’re killing me.”

“Hey, Dean,” Cas said, looking at Dean with a cocky smile. “The sooner you finish, the sooner maybe I’ll give you a preview of what you’re in store for tonight.”

“Wh-what would that entail?” Dean asked, flustered. Cas made a big show of licking his lips.

“Take a wild guess,” Cas said.

“Fuck,” Dean breathed out. “I can’t do this.” He stood up and walked swiftly over to Cas and settled on top of him.

“I knew I’d break you,” Cas giggled, wrapping his arms around Dean’s neck.

“I have work that I need to get done,” Dean said, “Important work.”

“Hm,” Cas hummed, pulling Dean in for a quick kiss. “Must be very important, seeing as you’re here, on the bed. With me.”

“Shut up,” Dean mumbled, smiling before diving back down to give Cas what he wanted and shoved his tongue down Cas’s throat.

~  ~  ~

“Mmh!” Cas moaned, looking at Dean with half lidded eyes. He smiled, swallowing the big forkful of spaghetti he’d just shoved into his mouth. Dean shifted in his seat for what felt like the millionth time, trying to find a comfortable position.

“Dean, are you okay?” Charlie asked, giving him a worried look. “You look sick.”

“Yeah, I’m good,” he responded, his voice breaking. “I’m just tired.” He looked back at Cas who was licking his lips suggestively and smirking. Dean had to clear his throat and shift again.

Charlie gave him another suspicious look. “Are you sure? You can’t sit still, you’re sweating, and you’re almost as pale as a ghost.”

“I’m fine,” Dean rasped. Cas hummed out another pleased noise, signaling to Benny he had done an amazing job with dinner. Dean glared at Cas from across the table and mouthed for him to stop. Cas only smirked and brought his fork up to his lips, exaggeratedly licking away the excess sauce. Dean had to bite the inside of his cheek to keep himself quiet.  

“Who wants dessert?” Benny asked, standing up gathering people’s plates. Cas shot his eyes over to Dean and gave him a grin.

“Here,” He said. “I’ll help you.”

“Thanks, Cas,” Benny said. Dean glared at him and shifted again to get comfortable. Cas leaned across the table and reached for Dean’s then Charlie’s plate. His shirt rode up just a little, exposing a sliver of his side. Dean saw the edge of something pink and lacey sitting high on his hips.

“Are you wearing—” Dean stopped himself. Cas smiled at him knowingly, confirming that yes, he was indeed wearing _panties_.

“Dean, are you sure you’re okay?” Charlie asked, nudging his shoulder. “You really don’t look well.”

“I’m fine,” Dean rasped, smiling nervously at his friends. “I’m just excited for dessert.” Charlie gave him a weird look, but left him alone to sit and go over what he’d seen when Cas reached over. _Cas is wearing_ panties, he thought, Cas _is wearing panties. Where did he even get them from?_

Dean looked over to the buffet just in time to see Cas bending over to get something. He felt like he could come right then and there; especially after Cas stood up and threw him a sly grin.

“Aye,” Jo called. He looked over as she sat down in the space Cas had been in.

“What’s up?” He asked, his voice higher than normal. He coughed and pretended as though he had something in his throat.

Jo eyed him. “You, uh… You okay?” She asked, a smile tugging at her lips. Dean smiled nervously again and nodded.

“Yeah,” he said, “Yeah, I’m good.”

“Really? ‘Cause you’re turning a little… _Pink_?” Jo smiled. Dean looked at her stupidly as his eyes widened in understanding.

“ _You_ got them for him?”

Jo winked and clicked her tongue, “You betcha,” she said, standing up again and laughing. “Well, have fun tonight.” She went and sat down next to Kevin and Sam. Dean stared after her, his mouth hanging open.

“Son of a bitch,” He mumbled to himself. Cas walked back over to the table with a plate in each hand. He smiled at Dean as he set a plate in front of Dean and then in his place.

“I’ll be right back,” he said, spinning around and sauntering away. He swayed his hips a little more than usual.

“Son of a bitch,” Dean mumbled to himself again. He was getting to the point of throwing Cas down on a table and taking him right then and there. Public decency be damned. “ _Son of a bitch!_ ” He looked back over to the buffets and saw Cas walking back with his shirt hiked up just slightly so if he moved in the right way Dean could see a flash of pink.

“I’m back,” he said, making to sit down in his spot. But Dean shot up out of his seat and stood right in front of Cas, leaning down to his ear and talking in a low voice so only he could hear.

“I’m going to fuck you so good tonight,” he said, reaching his hand behind Cas to pull up his shirt some more and finger the satin panties. “You’re going to be so far out of it, you’re not going to be able to say anything but my name. I’m gonna fuck you so good and hard the only thing you’re going to be able to remember is _me_. And the only thing you’re going to be able to focus on is my cock inside you, slamming into you over and over again with no rest. You got that?”

Cas let out a deep breath and wasn’t able to do anything but nod. Dean backed up and slid into his spot with a smirk. Now Cas was the one who looked flustered and out of it.

“Dean…” He said, eyes wide and glazing over with lust. “Now.”

“But I just got my pie,” Dean said, raising an eyebrow. Cas’s eyes widened in panic and he started to fidget.

“Please.” His voice came out strained and suspiciously like a whine. Dean chanced a look down at his groin and saw that a small bulge was beginning to form.

“Okay,” Dean said, smiling. He turned to the rest of the table. “Hey mates, Cas and I are gonna head out. We’re both a little tired.”

“Good night,” Jo said, giving Dean a quick wink before looking back at Kevin and laughing. The others nodded and made sounds of understanding, prompting Dean to get up and follow Cas out of the mess. As soon as they set foot on the main deck Cas pivoted and jumped Dean, kissing him hungrily and clawing at his clothes.

“Jo got you those panties, then, huh?” Dean asked, reaching his hand into the back of Cas’s trousers to smooth over the satiny fabric.

“Yeah,” he panted, closing his eyes and grabbing at Dean’s shirt. “Dean, please, c’mon. Take me to our room.”

“If you say so, baby,” Dean said, removing his hand from Cas’s pants to lift his legs up and carry Cas to their bedroom, kissing the whole way.

“Do you like them?” Cas asked, his voice catching just slightly as Dean dropped him on the edge of their bed. Dean smiled before slowly pushing Cas’s shirt up his torso and then getting rid of it all together.

“Do I like you in panties?” Dean asked, dropping to his knees and pulling Cas’s trousers off quickly. He looked at the panty clad boy in front of him with hungry eyes. “Angel, I’d like you in just about anything.”

“Just about anything?” Cas asked. He stretched his arms up and hooked his legs over Dean’s shoulders. “What wouldn’t you want to see me in?”

“Pft, that’s easy,” Dean said, “Another’s arms.” He smiled up at Cas.

“Shut up,” Cas giggled. Dean smiled wider before sliding his hands along Cas’s thighs and up his sides. Cas closed his eyes and melted into Dean’s touches. He felt Dean move closer and then the heat from Dean’s mouth on his length. “Oh, God,” he gasped, pushing his hips up slightly. Dean chuckled against him and hooked his fingers under the waistband of Cas’s panties.

Dean paused, “Do these…” he looked at the little bows on the sides of the panties and tugged slightly on one of the ribbons hanging down. It gave away a little and made one of the loops of the bow smaller. “These come undone?”

Cas nodded with his eyes closed, “Yeah, you can undo the bows and take them off or just take them off like regular panties.” Dean let out a long breath.

“Gods, you look so fucking amazing in these, Cas,” Dean said, hooking his thumbs back under the bows and pulling the pink satin fabric down just enough so that he could swallow down Cas’s cock.

“Dean!” Cas inhaled sharply, his hands coming to hold onto Dean’s hair as Dean’s mouth worked magic on his cock. “How do you do that?”

Dean smirked and pulled off, bringing one of his hands down to glide over Cas’s spit-slicked length. “Do what?” he asked, smirking when Cas had to fight for breath.

“Your mouth,” he got out, “H-how?”

“What about my mouth?” Dean prompted, flicking his tongue across Cas’s slit and collecting the precome that had started to bead there. Cas arched his back before spreading his legs and tugging harshly on Dean’s hair. Dean took Cas’s length back into his mouth and bobbed his head, drawing moan after moan from the boy. Cas pulled at Dean’s hair, making Dean grunt and moan around Cas’s cock.

“Oh!” Cas gasped, jerking his hips. “Dean, stop or I’m gonna come.” Dean pulled off with a pop and crawled up to kiss Cas.

“I have something for you,” he said, giving Cas a final peck before getting up and opening the drawer in his nightstand they kept the rope and oil in.

“Get your shirt off,” Cas whined, sitting up. Dean looked over his shoulder with an amused smiled as he got off the bed. He pulled his shirt off, shaking his head, and grabbed a small circular piece of leather.

“What that’s?” Cas asked, scrunching his eyebrows together.

“It’s a ring,” Dean answered, he came over to stand in front of Cas and unclasped it. “You put it around the base of your dick and it delays your orgasm until you take it off.”

“Would you wear it?” Cas asked, eyeing the ring with hungry eyes.

Dean smiled, “If you want me to,” he said. “But you can also wear it if you want.”

“Oh,” Cas was starting to breathe hard. “Would you… Would you tie me up while I was wearing it, too?”

Dean looked him up and down, his eyes stopping at his groin for just a second before going back up to his eyes. “If you want. Do you want me to?”

Cas bit his lip, “I-I mean, if _you_ wanted to I wouldn’t be opposed.”

“You’re so cute,” Dean laughed. “I think you forgot that you’re pretty much naked right now, baby. I can see just how much you want to be tied up and fucked with a cockring on.” Cas blushed hard, turning his face to look at the drawer in the nightstand where they kept the rope.

“Please?” He asked, blushing even harder. Dean smiled wider and leaned over Cas to kiss him.

“Arms _and_ legs?” Dean asked. Cas bit his lip again and nodded.

“Yeah,” Cas breathed out. “How long would you—” Cas cut himself off with a yelp as Dean pulled him up and spun him around. He made Cas get on his hands and knees on the edge of the bed before pulling him back by his hips into his cock. Dean smiled at the feel of the pink fabric against his length.

“You look so fucking good in these,” He said, grinding his hips against Cas’s ass.

“You think so?” Cas asked, biting his lip and holding back a moan.

“I know so,” Dean chuckled, pulling Cas back against him roughly. Cas turned to give him a cocky smile. Dean grinned back at him and shoved his hips forwards while pulling Cas back. The movement had Cas gasping in surprise and gripping onto the sheet beneath him.

“Dean, please?” He whined, pushing back against Dean again. “Please tie me up and fuck me. Gods, Dean, please; I want you in me right now.” Dean draped himself over Cas, holding him still as he lazily pushed his hips against Cas’s panty-clad and perfect ass.

“Not yet,” Dean said. Cas let out a desperate moan of Dean’s name. Dean shushed him with a harsh thrust before standing back up. He wrapped his arms around Cas’s waist and guided him onto his feet before he untied the bows on Cas’s panties and watched them fall to the floor.

“Dean,” Cas whined, leaning his head back against the man’s shoulder. “Please.”

“C’mere,” Dean said, turning Cas around as he backed up to his desk chair. He sat down and sucked Cas’s length into his mouth, bobbing his head a few times, before holding the ring out and looking up at Cas. “You sure you want to?” He asked, smiling comfortingly.

“Yes,” Cas nodded impatiently. “Put it on.”

“As you command,” Dean said, winking and then snapping the ring around him.

“Oh,” Cas gasped, “That’s tight.”

“Is it too tight?” Dean asked, looking up at him and pulling him closer by his hips.

“No,” Cas said, shaking his head. He brought his hands up and ran them through Dean’s hair. “It’s okay.”

“Perfect,” Dean said, rubbing circles against Cas’s hip bones with his thumbs. “I want you to try something new with me, okay?”

“Something more new than what we’re already doing?” Cas asked, cocking his head to the side and smiling. Dean smiled back and huffed out a laugh.

“I want you to try riding me,” Dean began, Cas opened his mouth to protest, but Dean cut him off. “Let me just show you, okay? We’ll stop immediately if it’s too much.” Dean pulled him onto his lap and ran his hands up and down the boy’s back.

“Okay,” Cas said, leaning back into Dean’s hands, “I trust you.” Dean smiled, and put his hand on the back of Cas’s neck to bring him in for a heated kiss. He pushed his tongue into Cas’s mouth and swirled it around Cas’s before pulling back. A line of spit connected their lips and only broke when they started laughing at it together.

“How much prep do you think you’ll need?” Dean asked, lifting his hips, still with Cas on top of him, to slide his trousers down to his knees. Cas ran his hands down Dean’s chest and kissed Dean again.

“Not much,” Cas said breathlessly, “I don’t know, you check.”

Dean chuckled, “Sit up.” Cas did as he was told and put his hands on Dean’s shoulders for leverage. Dean opened the nearest drawer of his desk and fumbled around in it until he found what he was looking for. He sucked and licked at Cas’s neck as he opened the small bottle of oil and coated his fingers.

“You keep oil in your desk?” Cas asked, throwing his head back when he felt Dean push a finger past his rim.

“Of course I do,” Dean said against Cas’s neck. “Ever since our little tryst in the mess, I’ve thought I should keep bottles around and one in my pocket when I’m with you.”

“Really?” Cas asked, pushing back onto Dean’s hand as a memory of Dean fucking him over one of the tables in the mess flashed behind his eyelids.

“Really,” Dean breathed out, kissing just under Cas’s jaw as he added another finger. He curled them just right, making Cas pitch forward and curl around Dean.

“Gods, Dean,” he gasped, “More please!”

“Hold your horses,” Dean huffed, scissoring his fingers to test how ready Cas was.

“No,” Cas huffed. “Just get on with it; I’m ready.”

“Hold on Cas,” Dean laughed. He pulled his fingers out and grabbed the oil, pouring it over his cock to the point of excess and guided Cas’s hips to be positioned over him. “Alright, slide down, but go at your own pace; I know it can be a little overwhelming for you, so you just focus on yourself, okay?”  

“Okay,” Cas nodded. He straightened his back and looked into Dean’s eyes as he started to slowly sink down on Dean’s cock. _“Oh, Dean!”_ He gasped, his mouth falling open and having a hard time keeping his eyes from closing. “You’re so _fucking_ big!”

“Hey, angel, hey just focus on my voice okay?” Dean soothed him, running his hands up Cas’s sides and over his thighs and hips. “You’re doing so good, baby, so good.” Dean paused to chuckle softly, “You don’t have to keep your eyes open, Cas, you know that right? You can close your eyes.”

“No,” Cas breathed out, “I want to see you.”

Dean smiled, “Okay, baby,” he said calmly. “You’re doing so good for me, Cas. You’re almost there, just a little more.”

“How much more?” Cas asked, letting out a surprised breath of air as the head of Dean’s cock slid past his prostate. He gritted his teeth, gripped Dean’s shoulders, and finally bottomed out with a quick spread of his legs.

“You’re there, baby,” Dean cooed, “Oh, baby, you did such a good job.” He kissed along Cas’s jaw and neck as Cas panted, trying to catch his breath.

“Dean,” Cas whimpered, wrapping his arms around Dean’s neck and burying his face into the hair on the side of his head. “It’s too much; I can’t move. I won’t be able to move.”

“Sh,” Dean whispered, placing small wet kisses on the crook of Cas’s neck. He wrapped his arms around Cas small, lithe body and held the boy as close to his chest as possible. “I want you to try a different approach to riding me, okay? But not yet. You need some time to catch your breath.”

“Yeah,” Cas gasped, clinging to Dean for all he was worth.

“You’re so beautiful, Cas,” Dean whispered, nuzzling his nose into Cas’ hair. “You take my breath away, Cas. Gods, I love you so much, you’re so perfect and amazing.”

“Thank you, Dean.” Cas took deep breaths, smiling at the feeling of Dean placing open mouthed kisses along his neck. “I’m ready.”

“No, Cas, don’t push yourself,” Dean said softly against Cas’s neck.

“I’m okay, Dean,” Cas sighed, lacing his hand into the hairs at the back of Dean’s hear. “Tell me what to do.”

“Cas,” Dean started, turning his head to capture Cas’s lips with his own. “Are you sure? We can wait a little longer, baby. We don’t need to rush.”

“No, Dean, I’m okay,” Cas said, pulling away to look into Dean’s eyes. “What do you want me to do?” Dean slid his hands down Cas’s sides to cradle his hips.

“Just,” Dean pushed him back slightly, “Just rock your hips.” Cas gasped as he felt Dean’s cock shift inside him. He moved his hips in the same way Dean had pushed him in and felt like he could faint.

“Gods,” Cas whimpered, “Oh gods, Dean.”

“Color?”

“Green,” Cas said, throwing his head back and rocking his hips faster into Dean’s. “Oh my gods, Dean! Oh… Oh! Fuck, oh!”

“It’s not too overwhelming?” Dean asked, running his hands over Cas’s thighs.

“Oh!” Cas yelped and stopped moving as Dean’s cock rubbed against his prostate. “Oh my gods!”

“Cas?” Dean asked, worry in his voice. He put his hands on Cas’s hips to stabilize him. “Cas, we can stop.” Cas breathed in deep, getting his bearings before looking Dean in the eyes.

“Just let me do do my thing,” Cas groaned in frustration and batted Dean’s hands away.

“Cas—”

“Sh,” Cas cut him off, rocking his hips forward and back slowly. His eyes fluttered shut and a smile tugged its was onto his face. “Feels so good.”

“It’s not to much?” Dean asked, a smile of his own spreading across his face.

“No,” Cas gasped, shaking his head and jerking his hips faster. Dean slid his hands up to Cas’s chest and ran his thumbs over the boy’s nipples, drinking up the loud and uncontrollable gasps and moans that left the boy’s lips.

“Gods, Cas,” Dean breathed out, raking his eyes up and down the boy’s body. “You look so...” He trailed off losing himself in the feeling of Cas moving faster and making the chair they were in slide back inch by inch.

“How — ah! — How does it feel f-for you, Dean?” Cas asked, his voice hitching every other word. Dean moved his hands down to Cas’s hips again and rubbed circles into his skin.

“Fuck, Cas,” he groaned, “So good.” Cas smiled wider and leaned forward to rest his forehead against Dean’s.

“Oh, Dean,” Cas moaned. He rocked his hips faster still and laughed at how Dean had to reach out to stop them from moving back any farther.

“Shit Cas,” Dean groaned, tilting his head up to kiss Cas desperately. Cas kissed back for a brief moment before he had to pull away to breathe. Dean kissed down to Cas’s neck, sucking bruises over his skin.

“Oh, Dean,” Cas whimpered, feeling heat start to pool in his abdomen. He tilted his head to give Dean more room on his neck and felt the man’s hands come to pinch at his nipples. Cas clung onto Dean as he started to shake and his hips stuttered. “Oh gods!” He felt something explode inside of him and he screamed out Dean’s name.

“Gods,” Dean said in a hoarse voice, digging his fingers into Cas’s hips as the boy whimpered and moaned while slowing his hips. “Cas… Did…” he paused, pulling back to look at Cas’s face. Dean let out a strangled laugh, almost coming then because of the absolutely blissed out face Cas was making. He was biting his lip and grinning dopily with his eyes closed. “Cas… I think you just had a prostate orgasm.”

“What’s that?” Cas sighed. He gasped and convulsed forward as he continued to rock his hips against lazily Dean’s. “Fu-uck!”

“Well stop moving if it’s too much,” Dean laughed, steadying Cas’s hips. Cas opened his eyes, giggling softly and trailing his hands down Dean’s arms to thread their fingers together.

“What’s a prostate orgasm?” He asked, grinning lazily and sighing quietly every now and then. Dean looked at him and smiled amusedly.

“You just had an orgasm, basically,” Dean explained, “But you didn’t ejaculate.”

“Oh,” Cas breathed out, still smiling. He moved his hips forward again and threw his head back while inhaling a stuttering breath. “Fuck!”

“Gods, Cas, stop moving if it’s that overwhelming,” Dean said, putting his hands on Cas’s hips and keeping him still. “Shit, baby. Are you that out of it?”

Cas sighed in frustration and pushed Dean’s hands away. “It’s not overwhelming,” he said. “It just feels so... So... _So_ good.” He rocked his hips again and moaned out Dean’s name.

“Gods,” Dean returned the boy’s moan with his own. “How the fuck do you manage to be so godsdamn arousing.” Cas gave him a toothy grin and rolled his hips sensually. “Fuck. Do you want me to take us to the bed?” Dean asked, already starting to get a grip on Cas and stand up.

“If you want,” Cas said, a laugh in his voice. Dean rolled his eyes and smiled fondly as he stood up, making Cas gasp and dig his fingers into Dean’s shoulders. “Gods, I’m so sensitive!”

“First time you’ve ever had a prostate orgasm,” Dean said, “It’ll do that to you.” He laid Cas down on his back and situated himself on his arm and knees. “I’m gonna pull out; are you ready?”

“Why do you have to leave?” Cas whined, his lips forming into a pout. “Why can’t you just make love to me right now?”

“Do you want to be tied up?” Dean asked, smiling. Cas sighed and nodded.

“Ready,” he said, “Do it real quick, like pulling off a bandage.”

“Cas, what? That’s insane,” Dean said, shaking his head. He shifted and put his hand on Cas’s stomach, pushing down. “Focus on my hand pressing into you, alright?”

“Alright,” Cas closed his eyes and focused on Dean’s hand as he started to apply more and more pressure.

“Okay,” Dean said, making Cas open his eyes. “I’m out. How’re you doing?”

“I didn’t even feel you pull out,” Cas said, looking down at Dean’s erection. He licked his lips and reached down to wrap his hand around his own cock. “Gods,” he gasped, arching his back as the feeling of immense pleasure coursed through him. “Dean!”

“You’re probably aching so bad right now,” Dean said, watching Cas’s hand pump over himself furiously.

“I wanna come so bad,” Cas whimpered, the hand he didn’t have on himself gripping onto the sheet beneath him. “Dean, please?”

“Stop touching yourself,” Dean said in a low voice. Cas shook his head, whimpering uncontrollably. Dean grabbed Cas’s wrists and slowly pushed them up to the pillows. “How do you want to be tied up?”

“I-I don’t want to be able to close my legs,” Cas clarified, biting his lip and thrusting up into Dean.

“Really?” Dean asked, smirking and meeting Cas’s thrusts with slow drags of his own. Cas cried out, struggling against Dean’s hold on his wrists. “Don’t move,” Dean growled into Cas’s ear, giving one last push against Cas’s before he got up. The bed dipped as Dean got off to grab the rope from the drawer.

He bent down to the floor, tying one end of rope to the foot of the bed by the nightstand before standing back up to walk to the other side of the bed to do the same.

“Why don’t you you just tie them to the bed posts?” Cas asked, gripping onto the pillows by his head to keep himself from reaching down and touching himself.

“If I did that,” Dean started, taking the other ends of the ropes and tie them in a figure eight. “Then you’d be able to close your legs; this way, because it’s close to the floor, it’ll almost be like your legs are tied down to the bed itself.” Dean lifted Cas’s leg, kissing his ankle as he slid his foot through both loops and then up to his knee. He situated one loop just above his knee while the other just below and then tightened it. “How does that feel?”

“Secure,” Cas answered. Dean nodded and headed back over to the other side of the bed to do the same to his other leg. “Why didn’t you just tie them around my knee? It bends, you know. It would’ve also been a lot easier.”

“I didn’t want to tie it around just your knee because that probably would’ve started hurting rather quickly and it would’ve left marks,” Dean grunted, leaning back down to tug the other end of the rope, pulling Cas’s leg into a bent position.

“Marks that I could’ve healed in a few seconds?” Cas asked, lifting his head to look up at Dean, smiling. Dean returned his smile.

“Trust me, the way I’ve done it will be more comfortable,” he said. “Do me a favor and push against the slats in the headboard as hard as you can while I tighten these? And tell me if it’s too much, okay?”

“Okay,” Cas answered. He put his hands against the headboard and locked his elbows. Dean pulled on the ropes until Cas was blushing from head to toe from the vulnerable position he was in.

“All good?” Dean asked, standing up and looking at Cas’s face. Cas nodded and Dean smiled. He reached back into the nightstand’s drawer and brought out a smaller length of rope to tie his hands up with, finishing in no time.

“It’s good, they’re not too tight,” Cas said, answering Dean’s question before he asked it. He smiled and came to stand at the foot of his bed, looking at Cas.

“To be square, Cas,” Dean said, pushing his trousers down to his ankles and kicking them off. “You look so fucking hot right now.” His eyes stopped on Cas’s as he started stroking his manhood. Cas tried to maintain eye contact with Dean, but ended up losing and darting his eyes down to Dean’s hand.

“Please,” Cas whined, pulling at his restraints. “Don’t tease me.”

“You spent the last three hours teasing me,” Dean said, giving him an amused look. “And you just had an amazing kind of orgasm. I think I’m entitled to a little teasing.”

“Please,” Cas whined again. Dean rolled his neck and crawled up to sit between Cas’s spread legs.

“Eh,” he said, shaking his head and smiling. “I think I deserve to make you squirm a little.”

Cas pouted, “No, please, I’m sorry. I won’t do that again.” Dean shook his head again, running his hands on the sensitive skin of Cas’s inner thighs.

“You won’t?” Dean whispered, leaning down and replacing his hands with his mouth.

“Dean, please,” Cas pleaded, trying to push himself into Dean with no avail.

“You know how long I can hold off my orgasm for,” Dean said, smiling before nipping at Cas’s skin. “But this time I can hit your prostate as much as I want, make you come time after time, without release.”

“Please,” Cas breathed out.

“You remember the safeword and colors?” Dean asked.

“Yeah,” Cas said, lifting his head to watch Dean move his mouth over his skin.

“Good,” Dean whispered, latching onto a sensitive spot he knew Cas had and sucking hard. Cas gasped loudly and whimpered.

“Please, Dean, please!” Cas begged. “Please, I’m sorry. I’m so sorry. I’m sorry for teasing you!”

“I’m not,” Dean said, nipping at Cas’s other thigh and kissing his way along the crease of Cas’s leg. “It lead to this, so…” He looked up at Cas as he placed another small kiss on Cas’s inner thigh.

“Please,” Cas whimpered. “I’m so hard.”

Dean smirked and hooked a finger under the head of Cas’s cock. “I know you are.”

Cas bit his lip and whined again. “Please!”

“Sh,” he said, coming up to kiss Cas. Dean sucked Cas’s bottom lip into his mouth and bit down lightly before pulling away. “I got you.” Dean sat back up and took Cas’s length in his hand.

“Oh!” Cas gasped in surprise, jerking his legs against the ropes. “Please!”

Dean chuckled, pumping his hand over Cas’s cock again. “Sh, Angel.” Cas shook his head, biting his lip and moaning softly. Dean smiled again and sped up his hand, making Cas writhe and pull against his bonds.

“I’m close,” Cas gasped, seconds later. Dean smiled happily, speeding his hand up even more and keeping his eyes on Cas’s face. His mouth morphed itself into the shape of an _O_ and his eyes snapped open, staring at the ceiling as his cock twitched in Dean’s hand and spurted out precome.

“You can’t come,” Dean said, pulling Cas’s gaze from the ceiling onto his face. “Remember? You won’t be able to come. It’ll just keep building and building and building… Until I take the ring off.” Dean slowed his hand down and then let Cas’s cock slap back against his body. He reached into the nightstand drawer for the oil. “How much time should I spend preparing you?”

“No!” Cas shook his head, his body trembling uncontrollably. “None!”

Dean shrugged, “I don’t know, Cas, I wouldn’t want to hurt you.” He dipped one finger into the oil and then pressed it up against Cas’s hole, circling around the rim until Cas was fighting for breath and pulling violently on his restraints. Dean pushed his finger past the ring of muscle, making Cas cry out.

Dean set a slow pace and kept at it until Cas was crying and begging him for more. Then, he pulled his finger out and dipped two back into the oil and pushed into Cas, once again. Cas arched his back and moaned Dean’s name.

“That good, huh?” Dean asked, adding a third finger. Cas’s thighs trembled and he moaned brokenly.

“Please!” He cried, trying to control his breathing. Dean pulled his fingers out and kissed up to Cas’s face.

“Color?” He asked, nibbling on Cas’s ear lobe.

“Green,” he whimpered. “Please?!”

“Sh,” Dean whispered, kissing the corners of his mouth. “You’re doing so good, baby, so good.”

“Uh huh,” Cas nodded, his chest rising and falling rapidly.

“Are you sure you want to still be tied up?” Dean asked, rubbing his hands over Cas’s stomach.

“Yeah,” Cas whispered, “Please.”

“Okay,” Dean said, nodding and sitting on his heels to oil his cock up. He guided himself to Cas’s entrance and pushed in slowly, earning a gasp from Cas.

“Gods Dean!” Cas heaved, fat tears falling from his eyes.

“It’s okay,” Dean huffed, thrusting into Cas slowly. “I got you.”

“So, so good,” Cas mewled. “You’re so big…” Cas trailed off, panting hard. Dean took pity on the boy and snapped his hips into Cas, angling them while he was at it to make the angel beneath him squirm.

A handful of thrusts into Cas’s prostate later, Cas snapped his eyes open and his mouth fell open in a silent scream. Cas’s hole clenched around Dean and he had to stop his hips from how tight Cas had gotten. Dean’s eyes widened as he realized what was happening. Cas’s eyes rolled up in his head and he convulsed around Dean. The pirate smiled and waited, letting the boy calm down.

Cas opened his eyes after a few minutes, taking a moment to focus on Dean. “Dean,” He whined.

“How was that one?”

Cas whimpered as another spasm coursed through his body. “I feel tingly… And… And so, _so_ good.”

“You want another one?” Dean asked, smiling wider.

“No,” Cas mewled, still breathing as if he’d just run a marathon. “No, please, I can’t take it.”

“Okay,” Dean said, leaning down and kissing Cas passionately. “Do you need me to take the ring off?”

Cas breathed out a sob. “No, do it when I get close, again.”

Dean nodded, kissing Cas again. “You betcha.”

“Wait!” Cas gasped, “Wait a second, though. Give me a second.” He closed his eyes and sucked in lungfuls of air for a few minutes while Dean smiled and massaged his sides, arms, legs, and stomach. “Green,” Cas finally said.

“Okay,” Dean said, “Are you sure you’re ready for this?”

Cas nodded his head, “Yeah.” Dean snapped his hips into Cas’s, pushing him up on the bed and making the boy cry out for all he was worth.

Cas yelled, throwing his head back and moaning loud enough that Dean was sure he’d be deaf by morning. “Dean! Dean! Dean, please!”

“Fuck Cas,” Dean grunted, moving his hips faster.

“Yes!” Cas screamed, arching his back off the bed. Dean growled and fucked into Cas even harder and faster, making sure to slam straight into his prostate. “Fuck, _Dean! ‘M coming!”_

“Just like that,” Dean said. He reached between them and unclasped the ring. Cas gasped in a stuttering breath.

He tensed up before coming over his stomach and screaming, “ _Dean_!”

“Fuck,” Dean grunted, feeling Cas clench around him almost unbearably tight. After a few stuttering thrusts, he came. He fell onto Cas’s and closed his eyes, savoring the feeling of _Cas_.

A few minutes later, Cas gasped, “Dean.” And pulled at the ropes around his wrists. “I wanna touch you.”

“Yeah,” Dean rasped, opening his eyes and smiling at the boy. He pulled out of Cas slowly, moaning Cas’s name as he did. Cas inhaled sharply and shuddered when Dean slipped out all the way. Dean undid Cas’s restraints, tossing them off the bed, and fell down beside Cas when he was done. Cas slowly let his legs straighten out as he panted. Dean turned his head to look at him and smiled. Cas looked so thoroughly fucked and sated, it made Dean’s chest swell with pride. “C’mere and I’ll massage your wrists.”

“How could I say no to that?” Cas yawned, rolling over and giving Dean his wrists. Dean kissed them and smoothed his thumbs over the red marks that were rapidly disappearing. “I love you, Dean.”

“I love you, too,” Dean responded, placing a lingering kiss on the top of Cas’s head before going back to his wrists.

“That felt—” Cas paused to yawn, “—so good, Dean.”

“Yeah?” Dean asked, smiling at the slur creeping its way into Cas’s words.

“Yeah,” Cas sighed deeply, “‘M s’ tired.”

“You _did_ just have, what? Two prostate orgasms and then an actual orgasm,” Dean said, “That’s gonna take a lot out of you.”

“Mh-hm,” Cas hummed. Dean pulled Cas closer into his side, kissing the top of the boy’s head.

“We’ll clean up in the morning,” Dean whispered, “Got to sleep, angel. I got you.” He turned onto his side to rest his forehead against Cas’s.

“Love you,” Cas breathed out, curling into Dean’s body and beginning to snore.

“I love you, too,” Dean responded, savoring the feeling of Cas’s cooling skin against his own as he fell asleep.

**Notes for the Chapter:**

> I hope you guys liked! Let me know what you thought about it and if you have any suggestions?


	13. Chapter Thirteen

**Summary for the Chapter:**

> Dean's been gone a long, long, long time. And it's killing Cas. 
> 
> Just when things are getting to a breaking point, Dean comes back.

**Notes for the Chapter:**

> So sorry this is two days late! We finally just started getting our new house ready to move in to and my mom's become a nightmare. Luckily I'm moving out in about a month or so, hopefully.

Chapter Thirteen

_March 30, 1694_

 

Dean had Cas pushed against the wall, and his hands all over the boy’s body. He had to leave in less than two hours, and Dean wanted to memorize everything Cas had to offer all over again. There was the possibility that Dean wouldn’t be able to come back for quite awhile. But Dean had planned out the collecting on, dealing out, and starting new Demon Deals down to the last day. That was the best he could to to make sure he wouldn’t be gone more than five months. Things happened, though, and there were smaller Deals he could carry out along on the way.

“How do you feel?” Dean asked, dipping his head to suck Cas’s bottom lip into his mouth briefly. Cas was breathing hard and his hands were on Dean’s neck and in his hair, tugging him impossibly closer. Dean pushed his hand into Cas’s drawers and started to jerk him furiously.

“Oh, more,” Cas whined, pushing his hips into Dean’s hand and crying out softly.

“Fuck, I love you, Cas,” Dean gasped as Cas tightened his grip.

“I’m coming,” Cas mewled. “Oh, I’m coming!” Dean watched Cas as he came because Cas always came _so_ beautifully… Dean felt himself fighting to catch his breath.

“You’re so beautiful, Cas, so fucking beautiful,” Dean said lowly, not removing his hand from Cas’s member. Cas moaned and threw his head back. He jerked his hips into Dean’s hand, coming a second time and calling out Dean’s name. “Just like that,” Dean whispered, cradling Cas’s cock in his palm and rubbing against Cas’s length slowly.

“Dean!” Cas gasped out, shaking as he was worked through his orgasms. Dean kissed Cas roughly, shoving his tongue into Cas’s mouth and, again, mapping out every inch of the boy’s mouth he could until he had to pull away for air.  

“So godsdamn beautiful, Cas,” Dean said as he started getting worked up again and moved his hand faster and rougher against Cas, fueled by the whiny gasps in Cas’s breathing he let out.

“Dean,” Cas whimpered, his hand shooting down onto Dean’s to stop him. “T-too sensitive.”

“Sorry,” Dean whispered, dragging his lips across Cas’s neck and up to his jaw. He kissed his way across Cas’s face before capturing Cas’s lips with his. It didn’t last long; both men needed air. But they didn’t want to stay separated for long and ended up pressing kisses to each other’s lips as they caught their breaths.  

When they were back to a more conscious and coherent state, Cas slid his hand down Dean’s front and palmed Dean’s erection, pushing away from the wall so he could switch their current positions. He dropped to his knees and tugged Dean’s trousers down enough to free Dean’s manhood. Dean inhaled deeply and ran his hand through Cas’s hair, watching as Cas enthusiastically took as much of his length into his mouth as he could.

Dean groaned, closing his eyes and letting himself relax into Cas’s touches. He could feel each and every one of his nerves on fire and his lungs start to burn from the limited supply of oxygen he was getting. The feeling of Cas’s mouth working over the head of his cock and his hands squeezing and pumping along his shaft was divine. Dean started repeating Cas’s name as if he was praying. “I’m gonna come, Cas,” he gasped, moaning loudly and gripping Cas’s hair. “I’m so close.”

Cas pulled off Dean’s length with a quiet pop, never stopping his hands, to speak. “It’s okay, Dean,” he said, kissing over Dean’s exposed tip. “Come for me?” Dean looked down to see Cas suck as much of his length as he could into his mouth. With that sight burned into his retinas, he felt his release start to bubble up in his abdomen almost painfully. Cas looked up at him through his lashes and bobbed his head faster, never breaking eye contact with Dean.

“Oh fuck!” Dean’s legs started to shake. “I’m coming!” He gripped onto Cas’s hair as he curled forward from the intense force of his orgasm. _“Fu-u-uck!”_ Cas moved one of his hands off Dean’s shaft and slid it to push against the man’s abdomen, drawing out a whine from Dean’s lips.

The sound Dean let out surprised Cas, and he couldn’t help but smile to himself. Dean had never been one to cry out like that and that it was _him_ that made Dean make that noise… Well…

Cas was still smiling as he swallowed all of Dean’s release and as he pulled off, stroking Dean’s length gingerly and coaxing him down from his high.

“You came so hard,” Cas stated, standing up and nuzzling into Dean’s neck as he gave Dean’s cock one last stroke that had Dean sighing deeply.

“Y-yeah,” Dean panted, wrapping his arms around Cas. “I think… I think I need to lie down.” Cas nodded, clasping his arms around Dean’s waist and helping to hold him up as they walked over to their bed. Dean collapsed onto the bed on his stomach. Cas smiled and crawled over to him, throwing one of his legs over Dean’s.

“How do you feel?” Cas asked, smiling only a little overly pleased with himself.

Dean coughed out a laugh. “Okay there,” he said, his voice coming out quiet. Closing his eyes, he concentrated on catching his breath. A smile tugged at the corner of his lips. “You don’t need to be cocky about this.”

Cas bit the inside of his cheek to stifle a laugh. “What ever could you mean, my love?”

“Shut up,” Dean said, huffing out a laugh. “Fuck; I’m gonna be sore for a week.”

“Yeah?” Cas asked, curling into the taller man’s side and scratching Dean’s back. “One could — and should — say, I’m the one who made you sore, too.”

“Oh, quiet,” Dean sighed, leaning forward to kiss Cas’s forearm. “I love you, Cas.”

“I love you, too, Dean,” Cas whispered, tracing small patterns into Dean’s shoulder blades. “We can’t fall asleep, though.”

“Mh-hm,” Dean hummed, already starting to doze off. Cas lifted his head to look at him and smiled softly.

“I—” Cas traced over Dean’s bottom lip. “—love—” He moved his hand and ghosted his thumb over Dean’s eyelid. “—you—” Then he placed a kiss on Dean’s temple. “—Dean.”

~  ~  ~

_May 29, 1694_

 

“Dean,” Benny started, his tone somewhat scolding. He sat down across the table from him in the mess. “It’s late, and I know you’re tired.”

“I’m not tired,” Dean said in a defensive tone. He shook his head to keep his eyes from closing.

“Yes, you are,” Benny insisted. Dean shook his head again. “C’mon, it’s time for bed.”

“I only have a few more deals to work on,” Dean said, concentrating on the words he was reading for a few second before they began to swim off the page. “I’ll be done soon, I promise.”

Benny sighed, “No. You’re done _now_. Dean, you’ve been staring at the same papers for the past two hours.”

Dean sighed in defeat. “You’re right,” he said.

“What’s troubling you so much, Dean?” Benny asked, taking the papers from Dean. “Is this about Ava?”

Dean snapped his head to look up at Benny. “No, of course not. C’mon!”

Benny rolled his eyes. Dean always forgot he couldn't lie to Benny. “You did the right thing, Dean,” he said. “Leaving her there on that island? That was the right thing.”

“No, Benny,” Dean sighed again. “It wasn’t. You’re just trying to make me feel better.”

“How am I doing?” Benny asked, clapping his hand on shoulder lightly, making Dean smile.

“You've done better,” Dean said. “But thank you.”

“For what it’s worth, I think leaving her there was the right thing. She did pull a knife on Cas. And threatened to expose you two. No one would believe it was true, but rumors hold power. And Michael would have just used it as leverage.”

“Thank you,” Dean said, making to stand up, but becoming dizzy and almost falling back down.

“Whoa there, brother,” Benny said, smiling a little. He grabbed onto Dean’s arm to help steady him. “Alright, yeah, you need to sleep.”

“Aye,” Dean grunted in response, gripping onto Benny as they made their way out of the mess.

Thanks to Benny, he made it to his cabin without falling flat in his face. Benny helped him to change into his night clothes and then bid him goodnight. Dean thanked him and then turned to his bed. He smiled when he saw Lisa and Ben there, sleeping peacefully. Not wanting to wake them, he carefully laid down on his bed. Dean immediately froze when Ben stirred.

“Dad,” He slurred, turning onto his back and grasping out to the side of the bed Dean usually slept on. “Dad?” Ben’s voice came out louder and clearer. He opened his eyes and sat up, beginning to cry. “Dad!”

“Hey,” Dean said calmly, “I’m over here bud.” He settled himself down and reached out to Ben.

“Dad,” Ben yawned with teary eyes, gripping onto Dean’s nightshirt and climbing onto his chest. “I had a bad dream.” Ben said, his voice small and laced with left over fear. “A sticky-monster was trying to eat me.”

“Well, I’m here now,” Dean answered, smiling as Ben nodded and rested his small head in Dean’s neck. “I’ll protect you.”

“Yeah,” Ben sighed, nodding again. “Dad?”

“Ben?” Dean asked, putting his hand on the boy’s back and rubbing it in circles. Ben lifted his head and kissed Dean’s cheek.

“I love you,” He whispered. Dean froze for a second before tilting his head down to kiss the top of Ben’s.

“I love you, too,” Dean whispered back, smiling like a sleepy idiot. “Now go back to sleep. I’ll keep the sticky-monster away.”

“Okay,” Ben yawned again. He settled down quickly, curled up in Dean’s side with his head on Dean’s shoulder.

~  ~  ~

_October 16, 1694_

 

Rumors of Dean “ _The Righteous Man_ ” Winchester of the Impala 67’s death had started to circulate throughout Heaven. Cas, of course, didn’t believe it. Not entirely, at least. Dean had been gone for almost seven months. Longer than he’s ever gone before and Cas was starting to worry. But he kept reminding himself that if Dean had been killed, then someone from the Impala would find a way to tell him.

But if the whole ship had been sunk, then there wouldn’t be anyone to get the word to Cas…

“Stop it,” Cas chided himself, pulling his covers up around him tightly. He couldn’t think like that. If Dean had really perished some other pirate would be taking credit for killing him and everyone on the Impala. Since no other buccaneer was, then there wasn’t any reason to believe the rumors of Dean’s death were true. And, anyway, the rumors originated from the old and crazy veteran sailors living on their broken down boats.

So, Cas came to the conclusion that no, Dean was not dead. He couldn’t be. And he wouldn’t die. Not out at sea and certainly not without Cas. He felt it in his bones that Dean was still alive. But there was always a doubt that maybe what he was taking for truth was just Cas wanting it to be truth so bad, he was tricking himself.

Cas kicked his covers off. He wasn’t going to be able to sleep; not yet. Getting up and slipping on some slippers, he walked out onto his terrace. The cool night air was nice and the breeze made him smile. He closed his eyes and breathed in deep. At times, Cas was content. Even if Dean was thousands of miles away. In this moment here, alone and fairly certain that Dean was alive and on his way back, Cas was happy.

But everything comes to an end; some things sooner than later. And this time that Cas was happy didn’t last long. The breeze died down, and Cas was left breathing stale air. The same air he’d been breathing his whole life.

Cas loathed Heaven. Everything about it left a feeling of something to be desired deep inside his soul. It was an itch he’d never been able to scratch until he’d met Dean. He couldn’t wait until Dean took him and whisked him away from this wretched place.

Cas hadn’t heard his father enter and was startled when he turned around and saw the man standing there with a stern look on his face. “Father?”

“I thought I’d told you to go to bed,” Michael said, looking Cas up and down as if he was covered head to toe in dirt.

“I-I couldn’t sleep,” Cas stuttered. “I just stepped out to get some fresh air.”

“Right,” Michael said, he stepped aside and let Cas pass to get into bed. “Well, I’ve come to tell you that the search for Ava has ended. I’ve had messages sent to all the neighboring towns that if she’s seen she’s a wanted woman.”

“Why wanted? What has she done?”

“She deserted her post. Maybe not a big deal to some, but I have to keep my reputation fierce. Maybe then Dean Winchester will stop coming to Heaven and once Crowley accepts my proposal then I can finally see that scoundrel killed.” Michael said, getting angrier with each word. Cas shrunk away from where he was on his bed and nodded.

“Yes father,” He said timidly. Michael set his jaw and walked over to his door, stopping in the frame and speaking over his shoulder.

“Go to bed, Castiel. A representative from the Kingdom is coming tomorrow to confer with us about that business proposal I talked to you about some time ago. I expect you to be up early and waiting outside my office by seven, do you understand?”

“Yes,” Cas responded, laying his head on his pillows. “Of course, father.” Michael shut his door and Cas heard his father’s heavy footsteps fade away. Cas sighed deeply, closing his eyes and thinking of Dean as he fell asleep.   

~  ~  ~

_October 24, 1694_

 

“What is it?” Dean asked, leaning in close to Charlie’s side. “It looks like another ship.”

“It is,” Charlie whispered. She handed the spyglass to Dean. “I’ve never seen those flags before.” Dean shot her a concerned look as he took the spyglass and held it up to his eye.

“Those are new flags,” he said slowly, studying the ship. “That ship is weak, though. It has many weak points. Tell Jo to load the cannons and Ash to help. We need to be ready. These are new pirates and they may be looking to pick a fight. Get everyone ready.”

“Aye, aye,” Charlie said, walking swiftly away to ring the alarm bell.

“If they do decided to attack then we need to be ready,” Dean said, nodding to himself as he heard the bell being sounded and then shouts from his crew to get ready.

“Captain,” he heard someone call. “Don’t forget about the Braedens.” Dean looked over his shoulder and dipped his head in thanks before turning and striding across his ship to get to his cabin, where Ben and Lisa were napping. He opened his cabin door and almost hit Lisa.

“Dean,” She said, sounding worried. “We heard a bell, what’s going on?”

“I need you two to stay in here, lock the door, and get cozy. There’s another ship coming our way,” He said, staying quiet so Ben wouldn’t hear him. “It’s probably nothing, but I want to be ready in case they decided to try their luck and attack. No matter what happens, do not unlock this door for anyone, okay? Not unless they say the code word.”

“Dean—”

“Poughkeepsie is the word,” Dean interrupted Lisa, giving her a look that meant she just needed to listen. “If they don’t say that word, then you _do not_ open this door. Is that clear?”

“Yes,” She said, nodding.

“Now, if you do hear someone at the door and they don’t say the code word, then you get into the closet and find the keyhole that this key goes to.” He handed her the key from around his neck. “It’s a passageway that leads to a secret room. Inside there’s an escape pod. It’s not like anything you’ve seen before; Gilda, Kevin, and Ash engineered it from some materials Gilda brought from her homeworld. It will take you to a house where you and Ben can live safely with an old friend. Use the code word. It’s to let him know you’re part of my crew and something has happened. He’ll help you.”

“Dean…”

“Now isn’t the time for that,” Dean said, shaking his head. He pulled Lisa into a hug. “I promised you would never be hurt on my ship, and I’m not going to break that promise.”

“Thank you,” Lisa whispered as she pulled away. Dean turned and stepped out of his cabin, giving her one last look.

“If worst comes to worst, know that I love you both, you understand?” He said. Lisa nodded, her eyes becoming wet. “Alright, now close the door, lock it, and keep yourselves safe.” She nodded again, slowly and hesitantly closing the door. Dean didn’t hear the locks click right away and let out a shaky breath. “Lock the door, Lisa,” He said. The first lock clicked not long later and then the rest followed — thirteen total. Twelve of which had never been used before this moment.

Dean closed his eyes for a second, collecting himself and his thoughts. “And Lisa?” He called.

“Yes?” Her muffled voice came from the other side of the door.

“If something does happen… Find a way to let Cas know, please? I can't just leave him wondering.”

“O-okay,” Lisa answered a moment later. “I promise.” Dean nodded, standing up straight before shrugging off his jacket and going to grab his sword and dagger. They had been specifically made for him. Bobby, the friend at the safe house, had given them to him.

The sword Dean called his _Demon Blade_ . It was straight and serrated from the hilt to two thirds of the way down the blade. It was a bitch of weapon to be killed with, honestly. You’d be in agony until the moment you died. The dagger Bobby said was called the _First Blade_. It was made from bone. Bobby said it was from the jaw of a donkey from ancient times he just had lying around, but Dean wasn’t entirely convinced of that.

He emerged from beneath the ship with his blades in their sheaths, ready to be drawn at any moment. Men and women from his crew were darting around, getting battle ready as he walked the length of his ship to check how close the other vessel was getting.

“Captain,” Chuck called, coming up beside Dean. “The ship has increased their speed; it seems as if they are going to attack.”

“Put up the sails,” Dean responded. “Red and white.”

“It’d be safer to just attack—”

“Safer, but not smarter. _We_ won’t be starting anything and I want them to know that; but we’re not going to go down without a fight if _they_ start something. Raise the white flag, and then red.”

“Aye, aye,” Chuck nodded, scurrying away to pass on the order. Dean stood, fiddling with his spyglass before taking it out and checking on the ship.

There was movement aboard, but nothing that alarmed him. No sails had been put up, which could be a good thing or a bad thing.

“Dean,” Sam said, coming up behind the captain. “On your order, everyone’s ready.”

“Aye,” Dean said. “Thank you, Sam.” He turned back to watch the ship as it sailed closer and closer. Sam stayed silent, checking his time keeper and then the ship every now and then. He was constantly gauging the amount of time it would take for them to reach the Impala.

“They should be pulling to port soon,” Sam announced after a while. “About five minutes with the speed they're at now. It could be later, seeing as they have to lay anchor.”

“Aye,” Dean said, nodding and turning around to descend onto the main deck in waiting. “Our anchor is set, I take it?” He asked, looking around at his crew in position.

“Aye, aye,” Sam responded. “They’re here.”

“Hm,” Dean hummed, nodding again. He stopped and planted his feet where he was, waiting for the smaller ship to glide to stop next to his Baby.

“Ahoy!” A female voice from the other ship yelled across to them. Dean slowly made his way to the opening where they lay the plank before responding.

“Aye!” He thundered, surprising even himself at the boom of his voice.

“Are ye’ Dean Winchester?” The voice asked. Dean narrowed his eyes and turned his head to call to sam.

“Have the bridge readied,” he said, turning back to cautiously survey the ship next to them. “Aye! I am Dean Winchester.” There was a long silence before anyone responded.

“May we come aboard?”

Dean thought for a moment. “Nay,” he yelled. “I don't think that's a bright idea. I don't know your name.” Another silence. Not as long as the first, though.

“My name is Abbadon,” the woman called. “I am the Captain of the Knights of Hell.”

“I haven't heard of you,” Dean called, “You’re new to the seas, then?”

“Aye,” she responded. “May we come aboard now?”

“Nay!” Dean rolled his eyes at her impatience. “I will lay our bridge and we will meet in the middle. If you try any funny business, my crew will not hesitate to start feeding the fishes with your crew.” Dean set his jaw and waited as the swabs started lowering the bridge. The other ship was smaller, and so the bridge had to be set at a slant, but Dean took this to be a good thing.

“Meet in the middle, no weapons?” Abbadon called over. Dean took off his weapons belt, handing it to Sam.

“Aye, aye,” he called back, starting to move onto the bridge, but was stopped by Sam’s arm on his elbow.

“Hey,” he said quietly, even though the other pirates wouldn't have been able to hear them. “You be careful, you hear me?”

“When am I not?” Dean asked, smirking. Sam let go of his arm and chuckled, shaking his head.

“Always,” he said under his breath as Dean started making his way along the bridge.

“It's nice to meet you,” Abbadon said, smiling lasciviously as Dean came to a stop. “Dean ‘ _The Righteous Man_ ’ Winchester.”

“Thank you,” Dean said, keeping his guard up. “Your ship is very…. Hefty.” Abbadon’s smile faltered.

“We’re new to the seas,” she explained. “We don't have much bounty…” she looked Dean up and down as if she was undressing him in her head. “Yet.”

Dean chuckled, “Should I feel threatened?”

“Oh,” Abbadon laughed. “No. I would never threaten, Dean Winchester.”

“No,” Dean said. “I don't supposed you would.” He looked over her shoulder, surveying how many hands he had on main deck at the moment. “How many in your care do you have?”

“Not many,” She said. “At least, not compared to your crew… Which I see lives up to the rumors.”

“Yes,” Dean breathed out. “All pirate crews are meager compared to mine. How great is yours compared to, let's say, the Hellhound Pirates?” He looked back at her. Abbadon laughed throatily before smiling dangerously and reaching behind her.

“Compared to the Hellhound Pirates,” she started, lowering her hand to her side, still keeping it hidden behind her thigh. “My crew is much stronger.” Abbadon swiped out at him with a hidden blade.

Dean leaned back just in time to dodge most of the damage the blade would have caused, but still was cut rather badly from his jaw to just over his right eye. Abbadon threw her arm out, punching him on the side of his face that didn't take the impact of the blade.

Dean did the same; he shot his arm out with his hand in a fist and knocked Abbadon off balance. She dropped the blade and it went falling into the water below them as she went sprawling out on her back. “I’ll give you one chance to _apologize_ , or I will attack.”

Abbadon sat up and spit out blood. She bared her teeth to Dean before launching herself up and at Dean, shouting as she went. “Never!”

“Sam!” Dean boomed, sidestepping the Abbadon and sending her stumbling onto her hands and knees.

“Fuck you!” She screeched and turned back, sweeping her leg out in hopes of knocking Dean off the bridge and to a watery death. Dean laughed as he grabbed a handful of her hair and tossed her down the bridge towards her own ship. The downward angle helped and she had to scramble to gain purchase.

“Go back to your ship and raise the white flag, or I will destroy you and your crew,” Dean said. “I'm giving you a second chance. _Take it_.”

“You’re not so scary, you know,” she said. “You’re just a little boy with an over glorified reputation.”

“Sweetie,” Dean laughed, walking over to her as she stood. “You’re about to find out just how wrong you are.” In a sudden movement he raised his leg and kicked her straight in the chest, sending her flying backward again as Dean turned and walked swiftly back to his ship. “ _Raise the bridge_!”

“Aye, aye!”

“Fucking amateur pirates,” Dean mumbled, wiping blood out of his eye before groaning at the sheer stupidity of the Knights of Hell.

 _“Dean!”_ Abbadon screamed, making Dean turn around and snarl at her. She raised her arm and a loud bang rang in everyone’s ears. Dean felt pain explode in his shoulder as the impact of the bullet jerked him back.

The next thing he knew there was an ear piercing boom and he was falling off the bridge, grabbing onto the wood just in time with his good arm before he plummeted into the quickly churning water below him.

“ _Dean_!” He heard multiple shouts call from the main deck before he felt several hands on his arms, pulling him back up.

“Faster!” Someone shouted. He felt himself be dragged back onto his ship as the dizziness settled in.

“He’s losing blood,” Dean heard a panics voice come from somewhere far away.

“The cut on his face…”

“...bullet hit an artery…”

“...Gilda!”

“Get me fixed,” Dean muttered as he lost consciousness and the ship rocked as another cannon was fired.   

~  ~  ~

_December 21, 1695_

 

“Have you been listening?” Michael asked, coming over to stand in front of the boy. A break had been called during one of Heaven’s meetings and Cas was supposed to read back the notes he'd taken while everything was in session.

“Yes, father,” Cas intoned. He held up his papers and began reading back what he'd written.

“Adequate,” Michael said. “We’re almost done for today.” He turned and slowly walked back to his desk in the courtroom. Cas nodded, feeling empty inside.

 _Nine months_ . Dean has been gone for nine godsdamn months. Three months short of a year since he's seen Dean. Since he's been able to hold him in his arms, kiss him, _touch_ him. Cas was desperately hoping for any news about his pirate.

He hadn't been able to get a good night's sleep in three months; he’d always wake up feeling like utter garbage. And his appetite had become almost nonexistent. It was a miracle he was able to function. He credited that to his Grace keeping him on two feet and replenishing the lack of sleep and nutrients in his body.

The question was: how much longer could his Grace keep this up? How much longer could _he_ keep this up?

And ever since that meeting with a representative from the Kingdom of Hell blew up in Michael’s face… Well, Cas’s Grace had more than just internal healing to do than normal.

“Castiel,” Michael’s voice cut through to him. “We're starting up again. Pay attention and take more than copious notes.”

“Of course, father,” Cas answered, no trace of emotion in his voice. He looked up at the woman on the stand now and jotted down key details of her testimony and anything that didn't line up with what had already been said by previous witnesses.

There had been a murder in one of the wealthier families of Heaven. The woman who had been killed was said to be having an affair with a poor merchant. When her husband — who happened to be a close and personal friend of Michael — came home and had seen them together, he allegedly killed them both.

Cas had been going over the case day and night — anything to kill time spent alone with his thoughts — and he'd found evidence to suggest that it was a double suicide.

A lawyer for the wealthy was trying to prove the husband innocent, while another lawyer was trying to prove the husband's guilt. If Cas cared even one ounce about this trial, he'd say that the husband’s lawyer was winning, but he honestly couldn't bring himself to give any empathy to the husband or witnesses.

Cas’s emotions were bottled up during the day; he saved them for at night when he would stand on his terrace and watch the sea in hopes of seeing the Impala. He hadn't, yet. But Cas still held hope.

“Your honor, we the jury are ready to announce our verdict.”

“Proceed.”

“We find the defendant: not guilty.”

Michael stood up, shaking the widowed husband’s hand and then the lawyers. He left his friend and his lawyer with a self-satisfied smirk on his face and came over to Cas.

“Congratulations, father,” Cas said, forcing a smile onto his face as he lied straight through his teeth. “You performed above expectations. I don’t think this case would’ve panned out in favor of your friend if you hadn’t been here.”

“Yes,” Michael said, “I do think the same.” He straightened his tie and coat. “We’re done for today, Castiel. Please gather your items and I’ll meet you in the carriage.”

“Absolutely father,” Cas said. Michael strided away to confer with some of his city employees. This court case was a nice vacation from Michael’s mayor duties, but he is still the mayor and has other duties to attend to.

Cas grabbed his things and headed out, smiling at his father's co-workers as he stepped his way carefully to the Novak carriage.

“Good evening, master Castiel,” the driver said, tipping his hat to him before looking forward again. Cas got into the carriage, settling himself into his normal spot and waiting for his father. He involuntarily let his mind wander to thinking about Dean and all the horrible _what if_ ’s that surrounded that topic.

 _Stop_ , Cas chided himself. He shook his head and forced himself to go over the trial that had just finished.

Naturally there were still some inconsistencies in the husband's testimony, but they didn't outweigh the evidence that proved him innocent.

One infraction that stood out to Cas was the time of which the husband said he got home. It didn't line up with the time in which it would've taken him to get home from the whorehouse. He said he left at around eleven fifteen, and his house was a twenty minute walk from the brothel. The husband said he got home at eleven forty, but he also said he took a carriage home; meaning he should have gotten home much faster.

The husband either had the driver stop at one of the taverns on the way back to get a few drinks, or he was lying about taking the carriage. However, the constable that helped him when he arrived at the police headquarters did say he smelled alcohol on the husband's breath. Meaning that inconsistency could be crossed off and the motive behind the husband lying about time of arrival and/or departure could be added.

“Castiel,” Michael greeted as the carriage door opened and he got in. “I have a meeting to go to at six tonight, so I will not be home for dinner.”

“Father,” Cas started, “It’s five o'clock now, would you rather not stay here instead of going back to the house only to leave again?”

“No,” Michael said, jolting forward as the carriage started moving. “I have to change and freshen up.”

“But father,” Cas forced out. “You look as handsome as ever. You have no need to change.”

Michael laughed, “Yes, I suppose so. But it is an important meeting.”

“Well, that explains it,” Cas said. Michael didn't respond, telling Cas that their conversation was over. They rode the rest of the way to the Novak residence in silence and when the carriage stopped, Cas made to get out but Michael stopped him.

“I do not know what's gotten into you as of late, but I like it. You're much more compliant with how you should be acting as a Novak. Well done,” he said, giving Cas a smile before getting out and gliding into the house. Cas sat in the carriage for a moment, feeling tears threaten to fall, before he got out.

Making his way up to his room slowly, he felt his cheeks become wet and he hurried into his room. He closed the door behind him, locked it, and then threw himself onto his bed, hearing something flutter and the fall to the ground from the gust of air that happened when landing on his bed. Cas lifted his head, crawling over to the edge of his mattress to see what had fallen.

It was a note. He picked it up with trembling fingers and turned it over, immediately recognizing the handwriting: _Dean_.

Cas tore the envelope open, fear and happiness making his gut wrench painfully.

“ _Cas ~_

 

_I’m back, angel. I’m so sorry for being gone so long. I swear it wasn't out of choice._

_Come see me when you can. I miss you._

 

_~ Dean_

 

_(P.S. I love you.) “_

 

Tears of happiness spilled out of his eyes and he ran to his terrace, looking out at the see and dropping to his knees when he saw the Impala docked

Cas ran out of his room and down the stairs, yelling to anyone who could hear him, “I’m going to the library!” He ran out the front door and sprinted to the docks. He stopped short when he reached the gate that marked the end of the heart of Heaven and fidgeted.

Looking around, he dashed into one of the alley ways and then made his way into the woods, running along the path he and Dean took in the early hours of the mornings after they’d woken up.

He breathed hard as he rushed onto the splintery wooden docks and up the stairs to the ropes. Cas didn't even think twice as he climbed himself onto the Impala, swinging himself over the ledge and landing with a thud and looking around.

“Where's Dean?” He asked, trying to catch his breath. Some of the crew looked at him with shocked eyes, some with anxiousness, and others with annoyance. Cas shook his head and ran into the mess, hoping to find Benny.

“Cas?” He heard Sam’s tell-tale voice ask as soon as he entered the room.

“Sam!” Cas yelled, running to hug the younger Winchester. “Oh god I missed you! I missed all of you so much!”

“Gods, Cas,” Sam laughed, hugging the smaller boy back tightly. “I missed you too.”

“Where is everyone?” Cas asked, pulling away and looked around Sam excitedly.

“They’re all on the quarterdeck,” he answered, nudging Cas back out of the mess. Cas beamed at him and walked out, running into Charlie.

“Cas!” she squealed, trapping him in a bear hug. “I missed you!”

“I missed you too!” Cas said, hugging Charlie tightly before look by up and seeing Benny, Gilda, Jo — everyone else. “You’re all here!” He almost cried, hugging everyone before looking around for Dean.

“Cas—”

“Where's Dean?” Cas asked, looking at everyone's faces. Fear gripped his heart. “What?”

“He's okay,” Gilda said, putting her hand on Cas’s shoulder. “There's just… You see...”

“What?” Cas insisted.

“We had a run-in with another pirate ship,” Benny started when no one else did. “They call themselves the Knights of Hell.”

“Where’s Dean?” Cas asked again, starting to feel panicked. No one answered, and instead looked behind Cas. A second later his voice came out, deep and rich — just as Cas remembered, but better; because this wasn't a memory, this was real life.

“Cas…”

“Dean,” Cas breathed out, smiling as he turned around and saw Dean. His smile fell immediately as he saw the man’s face and the nasty cut starting from one side of his face, and ending just above his eye on the left. “Dean?”

“It's okay,” he said, smiling. “It's healing nicely; thanks to Gilda and her magic powers.”

“What… What happened?” Cas asked, tears of both happiness that Dean was here, standing in front of him, and horror of what had happened to give Dean this horrible wound.

“I...” Dean started, he shook his head before rushing over and gripping Cas to him.

“Dean,” Cas sobbed, pulling on the back of Dean’s shirt to hold him tighter. “You’re here!”

“I am,” Dean said quietly, his voice shaky. “I’m so sorry, baby.” Cas sobbed out a laugh, shaking his head as he pulled away and crushed his lips to Dean’s.

“You’re here,” he whispered, smiling and kissing Dean again. “I missed you, Dean. I _missed_ you.”

“I missed you, too, Cas,” Dean breathed out, picking Cas up and ignoring the shooting pain he felt emanating from where he'd been shot. He tilted his head back to keep their lips connected as Cas was lifted higher. Cas wrapped his legs around Dean’s waist and kissed Dean desperately. “I love you, Cas.”

Cas smiled, resting his head against Dean’s when he had to stop kissing him to breathe. “I love you, too, Dean,” he whispered, smiling even wider. “I'm so happy you're back.”

“Me too,” Dean whispered, kissing Cas deeply again.

“Okay, okay, okay!” Jo interrupted them. She walked over and pushed Dean towards the door labeled _cabins_ . “Stop it. You’re being so mushy. Just, go _reunite_ in Dean’s cabin.”

“Jo!” Charlie scolded. But Dean was already carrying Cas away into their bedroom, pausing every few steps to sneak in some deep kisses.

Cas whispered, looking into Dean’s eyes as the man lowered them onto their bed, “Gods, I missed you so much.” He smiled for a second before frowning as his eyes traced the cut long Dean’s face. “What happened?” He asked, lightly running his finger over the red line. Gilda had obviously had to stitch up the cut where it ran over his cheek, bridge of his nose, and through his eyebrow. Cas closed his eyes, concentrating as he ran his fingers over the cut. When he opened his eyes, he smiled warmly.  

“That felt amazing. What… What did you do?” Dean asked, looking into Cas’s eyes.

“I healed the cut,” Cas explained, “Not all the way, but there definitely shouldn't be a scar when it's healed all the way now.” Dean smiled, leaning down and kissing Cas again in thanks.

“Fuck, Cas,” Dean gasped, “Fuck it feels so good to hold you again.”

“Yes,” Cas breathed out, nodding his head vigorously. He slid his hands down Dean’s arms until he could encircle the man’s wrists. “ _Touch_ me.” Cas moved Dean's hands under his shirt before letting go.

“Cas.” Dean hungrily splayed his hands on Cas’s torso, moving them up inch by inch and bringing the boy’s shirt to pool under his arms.

“Dean,” Cas moaned, arching his back into Dean. “I love you.” Dean kissed down to Cas’s neck, making sure to suck a few bruises into his skin before roughly pulling the boy’s shirt over his head and then moving down farther. “Oh my gods,” Cas whined, threading his hands into Dean’s hair.

“Missed you so fucking much, baby,” Dean muttered, sucking one of Cas’s nipples into his mouth and swirling his tongue around the sensitive bud until it was hard. After that, he moved to the other one.

“Dean, I'm not gonna last long,” Cas said, tugging on Dean’s hair and rocking his hips up into Dean as the pirate worked over his body. “I'm already so close.”

“I got you baby,” Dean huffed out. He reached between them and undid Cas’s pants, tugging them down just enough to get the boy’s cock out before sliding down Cas’s body and taking the length into his mouth. He bobbed his head like it was what he was born to do.

“Ah! Dean, slow down, or—” Cas cut himself off with a harsh gasp, “I'm gonna come.” Dean only moved his head faster, reaching up to play with Cas’s nipples. “I’m… I’m… I-I’m coming!” Cas heaved, coming hard enough that he wasn’t able to do anything _but_ come.

Dean moaned as Cas’s cum coated his tongue, making Cas shiver and release another spurt of cum into Dean’s mouth. Some of the boy’s release dribbled down Dean’s chin. He collected it onto his finger in one swipe and pushed the digit into Cas’s mouth. The boy eagerly sucked it away, biting down gently on Dean’s finger while he was at it.

“Gods,” Dean muttered kissing up Cas’s body before capturing his lips again. He smirked before quickly flipping Cas onto his stomach and pulling him onto his hands and knees. “ _I missed you_.” Dean dug his fingers into Cas’s hips.

Cas rocked back against Dean, smiling at the hardness he felt and eliciting a groan from deep in the man’s chest. “Fucking hell, Dean,” he gasped, pushing back to feel the hardness in Dean’s trousers again. “You’re so godsdamn big.”

“You sure know how to get me going, don’t you, angel,” Dean chuckled, pushing his hips forward to meet Cas’s movements. He hissed in pleasure and draped himself over Cas’s back, holding Cas to him and kissing the space between his shoulder blades before speaking again. “Never again,” he whispered. “Never again will I be gone that long.”

“Yes,” Cas agreed. He gasped as Dean yanked his trousers down even further, nudging him to lift his knees to pull the articles of clothing off all the way. After that, Cas heard the telltale sign of Dean’s buckle coming undone and the dip and shift of the bed as he shucked his own pants and shirts off.

“Fuck, angel,” Dean whispered, sucking his finger into his mouth and then circling Cas’s rim.

 _“Captain,”_ Cas moaned, pushing into the man’s touches. He heard Dean let out something that sounded like a growl and he trembled. “Oh, Captain.”

“Grab the oil,” Dean ordered, leaning over Cas’s back and kissing over his shoulder blades again.

“Yes,” Cas replied, smirking as he fumbled around in the nightstand drawer for the bottle of oil. Dean trailed kissed down Cas’s back as the boy placed the bottle in his outstretched hand.

“How often did you touch yourself while I was gone?” Dean asked, pushing Cas into the mattress by his neck and then going back to nip at and suck on the back of Cas’s thighs.

“Th-the first few months I-I-I came once every night,” Cas explained, gripping onto the sheets beneath him and smiling that he could grip _these_ sheets. The expensive silk sheets Dean insisted on because _‘it’s fucking hot when you rip holes in them,’_ Dean explained once.

“Yeah?” Dean husked.

“But then, I st-stopped and came o-on-only three times a week on av-average.”

“That so?” Dean asked. He flicked his tongue out against Cas’s rim, making the boy yelp and jerk forward before whining and pushing back against Dean.

“Again,” Cas breathed out, spreading his knees farther apart.

“Tell me what you were thinking about while you were touching yourself.”

Cas moaned, feeling the man’s tongue circle his sensitive rim, “I thought about you… Fucking me senseless; sometimes tied up, sometimes you held my legs open and told me not to move my arms. I thought about you putting that cock ring on me and then ordering me to ride you with my hands tied behind my back. Another time, it was the same fantasy, except you had me touching myself and I was begging to come, but you didn't let me — not until after you did.”

Dean hummed, “Maybe we’ll have to see about making those fantasies come true, yeah?”

“Gods yes, please Captain?” Cas whined. He let out a soft, breathy laugh when he felt his fingers rip through the sheets. Dean groaned, loud and rumbling, shoving his tongue deep into Cas’s hole with no warning. Cas yelled, arching his back as he heard the wet and sloppy noises Dean made as he fucked his tongue in and out of him. Every now and then he'd circle Cas’s rim, and then he'd shove his tongue back in while sucking and nipping at his rim.

Cas was a crying, whimpering mess when Dean finally flipped the boy back over. “Please?” He begged, “Please, I need you.”

“Sh,” Dean whispered, opening the bottle of oil and slicking up his fingers. As soon as he rubbed the pad of his finger against Cas’s rim Cas almost screamed, pushing down onto Dean’s hand.

“More, Dean,” he begged, rocking his hips down to meet Dean's hand. “More!”

“Bossy,” Dean mumbled, smiling as he added two more fingers at once. Cas’s eyes went wide and his mouth formed the perfect _O_ shape.

“So good,” he cooed, a toothy smile gracing his face and his breathing becoming ragged. “Been so long — too long.”

“Much too long,” Dean agreed distractedly. He was trying to find that little spot inside Cas to make him scream.

“Oh!” Cas gasped, shuddering as Dean rubbed past his prostate. “Th-there, Dean!”

“Where?” Dean smirked, pushing against the bundle of nerves again. “Here?”

“Yes!” Cas yelled, moving his hips down in harsh jerking movements. “Dean please! I need you!”

“What do you want Cas?” Dean asked, feeling his own cock start to ache. Cas pushed Dean’s hand away roughly and sneered.

“Fuck you, Dean,” he growled, bolting up and pushing Dean down onto the bed.

“Gods,” Dean gasped in surprise as Cas climbed on top of him and snatched the oil out of his hand.

“I said,” he said through gritted teeth, “I _need_ you.” Cas fumbled to oil Dean’s cock and then smirked as he immediately sunk down on it.

“Fuck!” Dean gaped, grabbing onto Cas’s thighs. “Oh my gods, Cas. Fucking hell!”

“I've been practicing, Dean,” Cas teased. He lifted himself up and dropped back down, letting out a pleased huff. “You know what I did?” he put his hands on Dean’s chest for leverage. “I used that gold you gave me — you know, when you thought I was a whore — and I went into the town market.” Cas rotated his hips, making Dean gasp for breath. “I bought another toy for myself.”

“C-Cas,” Dean rasped, throwing his head back and moaning loudly.

“It's not as big as you,” Cas continued. He let out an almost pained whimper before sharply inhaling and lifting himself up again. “But it’s adequate.” He dropped back down, drawing a stifled shout from Dean’s lips. Cas smirked and started really fucking himself on Dean’s length.

“Fuck!” Dean grunted, “I’m gonna come.” Cas stopped his movements and rolled them over, wrapping his arms and legs around Dean.

“C’mon then, _Captain_ ,” he growled into Dean’s ear, digging his nails into the man’s back as Dean started to move his hips at a fast, punishing pace. Cas clung to Dean, taking big, gasping breaths.

Dean’s hips stuttered and he grunted, “S-sorry.” Before he angled them, slamming into Cas and coming just as Cas also tensed up and cried out Dean’s name.

“Dean,” Cas heaved out, saying it like he would a prayer. “I… I love… you.”

“I love you, too,” Dean panted, lifting his head and kissing over Cas’s face.

“Dean… Oh my gods… I haven't—” he convulsed, “—come so hard in forever.”

“Fuck,” Dean groaned, giving one final thrust before pulling out and smiling. “Me too, angel, me too.”

 _“‘Angel,’”_ Cas repeated, a dopey smile coming onto his face. “I missed you… I missed your voice, your face, your presence…”

“My dick,” Dean laughed.

“Of course,” Cas said, giggling. He craned his neck forward and latched onto Dean’s neck, sucking a dark purple bruise into his skin. He wanted this one to hurt a little bit for Dean and for it to last a while.

“Damn, Cas,” Dean said breathlessly. He rolled off Cas, dragging the boy across the bed into his side. Cas curled up into him and threw a leg over his waist. “I love you, angel. I can’t say it enough, squarely,” Dean said, turning his head to nuzzle into Cas’s hair.

“I love you, too,” Cas nodded. “Rumors went around that you’d died. I didn’t believe them; not fully, at least… I didn’t want to believe them.”

Dean whispered, “I would never leave you, Cas… Never. You’re...” he paused, turning on his side to cup Cas’s face. “You’re my everything. I promise, when the time is right, I’m going to take you away from your father and everyone who’s ever hurt you. You’re my future. And everything that I have or will have… Cas, it’s yours.”

“I love you,” Cas said, biting his lip to keep himself from crying. “I love you Dean Winchester.” He crushed his mouth to Dean’s and threaded his hands into Dean’s hair, pulling the man’s mouth impossibly closer to his own. He slid onto Dean, digging his knees into the bed on either side of Dean’s hips. Dean held Cas to him tightly and laughed lightly as their teeth clacked together from the force of Cas’s grip in his haid.

“I’m not going anywhere,” Dean managed to get out between kisses. “I love you.” He moved from Cas’s lips to the boy’s jaw and then to his neck, tracing his tongue along the hollow of Cas’s throat. Cas closed his eyes and tilted his head back. He started moving his hips in figure eights and pulling on Dean’s hair enough to make him sigh against his neck.

“I want you—” Cas interrupted himself as he moaned. “—I want you to fuck me. I don’t want you to make love to me, I want you to _fuck_ me. I want you to fuck me hard enough for it to hurt. I want to be able to feel it for days to come.”

“Cas,” Dean said, the word holding an intense amount of heat. “I’ll fuck you, alright. I’ll fuck you good and hard.” He quickly flipped them so Cas was beneath him and then he pushed Cas onto his stomach on the bed, pulling him onto his hands and knees in one swift movement. “I’ll fuck you so good you won’t be walking right for _weeks_.”

“Yes,” Cas breathed out. “Yes, please.”

“Mhm,” Dean hummed, reached down and grasping Cas’s cock in his hand. “It feels so good to be able to touch you again, you know.”

“Yes,” Cas repeated, pushing back to feel Dean’s own growing erection. He smiled and spread his knees farther apart, gripping onto the sheets below him. “So fucking good.”

“What a sailor’s mouth you’ve acquired,” Dean said, feigning shock. He let go of Cas’s length and moved his hand to circle the boy’s rim. “I have no idea where you could have possibly picked that up.” Cas laughed breathily as Dean slid his fingers into him. “Who fucking knows. I’m a little too preoccupied by other things to care, squarely,” Dean finished, smiling widely and pulling his fingers out before grabbing the bottle of oil and coating his shaft in it. He lined the head of his cock up with Cas’s hole before moving his hands to the boy’s hips.

“C’mon, Dean,” Cas barked, looking back at Dean with lust filled eyes. “Fuck me.”

“If you insist,” Dean said, shrugging. He gripped Cas’s hips roughly and pulled the boy back as he thrust forward.

“Fuck!” Cas yelped, moaning Dean’s name loudly as the man started fucking into him, pulling him back by his hips as he thrust forward — hard. He threw his head back as moans were punched from his lungs with every pull and push of hips. “Harder!”

“You want it harder?” Dean asked, a hint of disbelief in his voice.

“C’mon, _Captain_ ,” Cas growled, looking back at the man. “Do I need to say it again?” He smiled at Dean cockily.

“Not at all,” Dean said, moving his hands to cup Cas’s shoulders. “You sure you’re ready for this?”

“Dean! Fuck me like you actually want me to come,” Cas said, a bit of annoyance laced in his words.

“Okay,” Dean said, gritting his teeth. Cas began to smile but was stopped as Dean drove his hips forward.

“Oh, my gods!” His arms gave out as Dean fucked right into his prostate; the only thing holding him up was Dean. Cas gasped for breath as Dean continued to move his hips hard enough that Cas was sure he wouldn’t be able to sit right from the way Dean’s hips were slamming into him.

Dean craned his head to snarl right into Cas’s ear, “This hard enough for you?” He punctuated his sentence with another snap of his hips. Cas hung his head, whimpering in answer to Dean’s question. He felt his orgasm building faster than he thought possible.

“Dean,” Cas gasped in a moment of clarity. “Don’t stop!”

“Wasn’t planning on it,” Dean huffed, fucking into Cas even harder.

“Oh, my gods! Don’t stop!” Cas screamed, throwing his head back as he came, “Please don’t stop!” He went rigid, gasping and clawing at the bed sheets beneath him. “Fuck! Don’t stop!”

“Gods,” Dean groaned out. He held Cas to him tightly, snapping his hips forward into Cas’s prostate over and over again. Cas shuddered and moaned out as he came again. “Fuck! Did you just come again?”

“Fu-u-uck!” Cas whimpered between thrusts, his voice gone hoarse. Dean breathed out a laugh and kept fucking into Cas.

“That’s right,” Dean praised. “Come for your Captain.” Cas seized up violently, clenching down on Dean. He screamed Dean’s name as another orgasm ripped through him, shooting white hot bursts of pleasure through Cas’s entire body and making every inch of him shake enough that even Dean could feel it. “Fuck,” Dean moaned as he spilled himself inside Cas a moment later when Cas’s rim fluttered around his cock. He thrust through both of their highs, only stopping when Cas whimpered.

Dean gingerly pulled out of Cas and laid the still trembling boy him down on his back on the mattress. Cas breathed hard and let out pitiful little whines with each breath. The muscles in his stomach twitched as tried to relax. “De—” he hiccuped, sounding as though he was still getting fucked. “—an.”

“Baby,” Dean soothed, coming to sit between Cas’s legs. He reached into another drawer of his nightstand and pulled out a small can of lotion. “I’m gonna take care of you.” Dean opened the bottle and tapped the opening on his palm. Once there was enough he dropped the bottle beside him and rubbed the lotion onto Cas’s stomach.

“Hm,” Cas moaned loudly. His eyes rolled up into his head. Dean crooked an eyebrow up in disbelief.

“Are you… Are you still coming?” He asked, kneading his fingers into Cas’s stomach and letting out a breathy laugh as he felt the boy’s muscles twitching and spasming. “No,” Dean said, digging the palms of his hands into Cas’s abdomen. “Not coming, exactly. But you’re not _not_ coming.” Cas whined, clenching his fists around the sheets beneath him. He mumbled out incoherent words and thoughts as Dean massaged the soothing lotion into his skin. Dean smiled and listened to his angel’s nonsensical chatter, still loving every sound that came from the boy’s mouth.

When Dean felt Cas’s muscles calm, he crawled up Cas’s body and kissed him. “Sh, baby, you don’t have to keep telling me. I understand.” He said. Cas tried to move his lips against Dean’s, slurring out something that Dean deciphered as _‘I love you.’_

“I love you, too, Cas,” he replied, giving the boy one last kiss before settling down and cuddling close to his angel.

**Notes for the Chapter:**

> Let me know what you think?


	14. Chapter Fourteen

**Summary for the Chapter:**

> Dean's birthday has come around and he's agreed to celebrate it for the first time in over ten years. Cas and the crew have something special planned to show Dean that everything he ever knew about birthdays is wrong.

**Notes for the Chapter:**

> Sorry this is so late! Lots of drama came up at once.

Chapter Fourteen

_ January 24, 1695 _

 

“Wakey, wakey,” Cas whispered. It was the morning of Dean’s twenty-ninth birthday. The first one Cas got to celebrate with the man. Needless to say, he was excited. But Cas didn’t want to do anything too fast or too soon and freak Dean out. He was going to take things slow today. “How are you feeling?” 

Dean groaned, “Tired.” He rolled onto his stomach, turning his head so he could crack an eye open to look at Cas. “What time is it?” 

“It’s ten,” Cas responded, laying his head down on the side of the pillow Dean’s wasn’t. “We’ve got a little time before we need to get up and eat.”

“Good,” Dean said, smiling as he closed his eye again. “How long have you been up?” 

“Not too long,” Cas responded, reaching up to trace his finger along the arch of Dean’s brow. The man cracked an eye open for a second before closing it again. 

“You got dressed?” 

“I did,” Cas whispered. He trailed his hand down to thumb over Dean’s lips. “I wanted to talk to you, though.” 

“Hm?” Dean hummed. “What about?” 

“Today…” Cas started slowly, pushing a hand through Dean’s hair before trailing it down to scratch the man’s back soothingly. “...is your birthday.” 

“So?” Dean stiffened slightly. 

“ _ So _ … I’ve got something…” Cas bit his lip and pushed himself closer to Dean. “ _ Fun _ planned for you tonight.” He hummed, “That is… If you’re interested.” 

“Oh?” Dean started, he pushed himself up onto his elbows, looking at Cas. “Depends on what it is.” 

“I can’t just tell you,” Cas said, feigning exasperation. He nudged Dean to lift his arm in order to slide under him. “That would ruin the surprise.” 

“Well,” Dean smirked. “Maybe there’s something I can do to persuade you to tell me?” He started to move his hands down Cas’s body. 

“Ah-ah-ah,” Cas pulled his hands back up by his wrists. “Nope. Not right now, old man.” 

“I’m only twenty-nine,” Dean defended himself. “And why not? It’s my birthday today. Shouldn’t I get whatever I want?” 

“Aye aye, Captain. But later,” Cas giggled, pushing Dean up and off the bed. “Get dressed. Benny’s prepared a special breakfast for you.” 

“Did you ask him to do that?” Dean asked, smiling as he walked over to his dresser. 

“No, this was Benny’s idea,” Cas said, sitting up. He watched Dean as he got dressed, adoring the way he moved. Everything he did seemed calm and calculated. It still amazed Cas how fluid his motions were and how attractive he could make putting on a shirt. 

“I can feel you staring, you know,” Dean said, turning around as he tied his pants. 

“Sorry,” Cas whispered. He blushed, throwing the sheets off of him and quickly walking over to Dean. He snaked his arms around his torso and felt Dean’s arms come to quickly wrap around himself. Cas buried his face in Dean’s chest, inhaling slowly before exhaling out the words, “I love you.” 

“I love you, too,” Dean said into Cas’s hair. He hugged Cas tighter and smiled, rocking them to the sound of imagined music. 

The two pulled back after what seemed like forever and Cas stood on his tiptoes while Dean bent over to meet Cas halfway in a slow, tender, and passionate kiss. Their lips moved against each other's automatically. They no longer had to think about what to do. It was like breathing now. 

A knock at their door had Cas jumping away from Dean and blushing. 

“Breakfast,” he mumbled, trailing his eyes down from Dean’s face to his chest in an almost longing way before snapping himself out of it. “We’re coming,” Cas called as he grabbed Dean’s hand and pulled the man with him to the door. 

Dean groaned as he trudged behind Cas, “Food isn't really what I'm hungry for.” He shook his hand from Cas’s to wrap his arms around the boy’s middle. Cas smiled and opened the door, trying to walk out of their room with Dean pulling him back into his broad chest. 

“It's hard to walk like this, Dean,” Cas complained, only getting a soft grunt from his partner. Dean didn't let go, still; and instead he sweeped Cas off the ground with one arm cradling his back while the other was under the boy’s knees. Cas clasped his hands together behind Dean’s neck and yelped in surprise. 

“You looked too tired to walk,” Dean excused himself, nuzzling into the hair above Cas’s ear with a big smile. 

“I’m perfectly fine to walk,” Cas laughed as Dean stepped out into the hallway, making his way to the mess. 

“Eh,” he mumbled, turning to push open the door onto the main deck. “It was making  _ me  _ tired, then.” 

“You’re ridiculous, Dean,” Cas giggled, pecking the man’s cheek before resting his head on Dean’s shoulder. Dean only smiled and continued his journey to the mess, nodding a ‘good morning’ at his hardworking mates as they passed. 

When Dean walked into the mess he almost dropped Cas. It hadn't been changed much, but a few colorful strips of dyed fabric hung from the ceiling and there was colored glass placed around some of the lights that basked the whole room in a pleasant light blue glow. 

Cas lifted his head and whispered hopefully, “Do you like it? We didn't want to go overboard but it's not to plain?” 

“It's…” Dean looked around with wide eyes. He set Cas down and took a few tentative steps forward. A few memories of his previous birthdays flashed through his brain making him start to breathe heavily and feel trapped. Part of him was saying run; run and don’t look back. But Cas came up behind him and placed a gentle hand in the middle of his back. 

“I’m here,” Cas said softly, his other hand came to rest on his arm. He spread his fingers out and nudged him forward, keeping himself close to Dean. 

“It’s…” Dean tried again, swallowing a lump in his throat. “This is much different than what I remember birthdays being.” 

“Those weren't birthdays,” Cas whispered, gripping Dean’s arm tighter; as if he was plagued by the awful memories of Dean’s past instead of Dean. “Here… You’re surrounded by the people who love you.” 

“And love you, we do,” Charlie interrupted, stepping up behind the two and giving Dean a hug. “Happy birthday.”

“Thank you,” Dean said quietly, hugging Charlie tightly. After he pulled away, Dean was bombarded with hugs and wishes of  _ happy birthday _ . 

The last to come up and hug him was Sam; who handed Dean a small rectangular item wrapped in cloth. “Happy birthday, Dean.” 

He smiled warmly at his older brother and motioned for him to open it. Dean eyed the present carefully as he pulled the string tied around it until the fabric fell open. He furrowed his eyebrows together at the stained wood box for a second before flipping it open.

He stared at the new and pristine looking spyglass carefully set in some more cloth. Looking up at Sam he said, “You got me a new spyglass?” 

“Not just any spyglass,” Kevin said, “I spent a week or so working on that to make it so you have multiple lenses that enhance how far you can see.” 

“Really?” Dean asked, sliding back the lid to reveal the polished, shiny, and gold cylinder. “Wow.” 

“It's actually from all of us,” Sam said. 

“Do you like it?” Charlie asked hopefully. 

“I love it,” Dean said. He looked at all of his mates and smiled gratefully. “Thank you.”

“Don't mention it,” Charlie said, “Turn around though. Benny made something special for your birthday.” 

“What’s more special than his  _ Pig ‘n a Poke?” _ Dean joked, turning around as he spoke. The sight he was greeted with made him almost drop the spyglass and Cas giggled before taking it out of his hand. “I’m dreaming, aren't I?” 

“Nope,” Benny laughed as he came out of the kitchen with another pie. “I've made breakfast, lunch, dinner, and dessert. All as pies.” 

“You’re kidding?” Dean asked, a little bit of awe in his voice. 

“Not in the least,” Benny chuckled. He motioned towards the table full of different kinds of breakfast pies; and Dean was the first one to sit down, practically drooling at all the different options there were. 

Cas smiled at how happy Dean looked, filling his plate with a slice from as many of the dishes as he could. He sat down across from the Captain and felt an overwhelming surge of warmth flow through his body. This was Dean…  _ Happy  _ on his birthday. 

 

~~~

 

As Dean opened the door to their cabin Cas whispered, “May I give you my present now?”

“If it's more food I don't think I could eat it. I’m stuffed,” Dean said, holding a hand over his stomach. Cas laughed a little as he entered their room and shook his head. 

“No, it's not food. I can't cook or bake for the life of me,” he said, smiling. “It’s more of an  _ activity _ .” 

Dean raised an eyebrow. “Oh?” He smiled as he snaked his arms around Cas’s middle and lifted him up. “Then by all means… Please give me my present.” Dean started to move towards the bed but Cas stopped him. 

“Not yet,” he said, wriggling out of Dean’s grip and onto the floor. “Close your eyes.” 

“What are you—?” 

“Do you trust me, Dean?” Cas asked, cupping Dean’s face with one hand while resting the other over the man’s heart. 

Dean looked at Cas and smiled softly. “Of course I do.” 

Cas smiled back and whispered, “Then close your eyes and let me give you your present.” 

“Oh, okay…” Dean closed his eyes, straightening his back. “If it's a—”

“Hush, Dean,” Cas said softly. “Let me do this for you.” He slipped his hands down to undo the first button of Dean’s shirt, kissing the newly exposed skin. Slowly and methodically, Cas went about undoing the rest, placing kisses as he went. 

He ran his hands up Dean’s chest, opening his shirt and pushed it off Dean’s shoulders. 

“Cas, what are you doing?”

“Don't talk Dean,” Cas whispered, kissing the man’s collar bones before dragging his lips across Dean’s skin slowly. “Let yourself feel everything I'm doing, okay?” 

“Okay,” Dean’s voice came out barely above a whisper. Cas ran his hands over Dean’s shoulders and shoulder blades first, and the down Dean’s arms—his heart squeezing at all the scars he saw on them. He followed his touches with light kisses. After he reached Dean’s wrists he stopped, taking Dean’s right hand and bringing it up to his mouth, turning it over and kissing right in the middle of his palm before lacing his fingers with Dean's. He turned around so his back was against Dean’s chest, pulling the man’s broad arms around him and turning his head to nuzzle into Dean’s neck. “Sometimes, I can’t believe I’m the one that gets to love you…” Cas whispered into the skin where Dean’s neck and shoulder met. “Other times I can't believe you love me back.” 

“I do love you,” Dean couldn't help himself from whispering. Cas spun back around to face Dean. 

“When I look at you… Dean, I feel like I'm looking into the sun.” Cas took his hands from Dean’s and walked around to kiss the man’s back. “You’re the single most beautiful being I've ever seen.” 

Dean let out a choked laugh before he started to protest, “I’m not—”

“You  _ are _ ,” Cas said with finality. He traced the edges of the scar along Dean’s spine. “All these rough edges and blemishes on your skin… You’re still beautiful even though you have them. You’re stunning, Dean.” Cas lifted himself onto his toes to kiss the back of Dean’s neck where Alastair’s disgusting excuse of a  _ “present”  _ started. “You’re above beauty.”

“Cas...” Dean’s voice was shaky. 

“You’re still growing,” Cas spoke into Dean’s skin. “Improving… Molding yourself into a better man.” He came to stop his hands where the scar did and he slid them to encircle Dean’s waist, massaging his palms into the man’s abdomen. “It’s hard to believe that you let me help you with that.” Cas placed a tender kiss right in the middle of Dean’s back; where Alastair had cut him the deepest. “I love you, Dean.”

“ _ Cas _ .” 

“I know sometimes you don't think you're a good person or that you're not enough for me… But Dean, you are enough. You’re so much more than enough.” Cas came around to face Dean again. He undid the string keeping Dean’s trousers up and helped Dean to step out of them. But he didn't stand up, and instead he sat on his knees, running his hands over Dean’s legs and closing his eyes. “I know you think these scars you have…” Cas started, feeling his heart clench again at all the variations of skin he could feel on Dean’s legs. “...make up who you are, and that who you are is an ugly and unlovable person. But that's  _ just not true _ , Dean.” 

“I—” 

“No,” Cas interrupted again. “Listen to me, and if that's not enough, feel my touches.” He stood up, keeping his hands flat against Dean’s body. “Every time I touch you, Dean Winchester, it's like the first time all over again. My heart stops and all logical thought vanishes from my mind.” Cas grabbed Dean’s wrists lightly and guided them to his hips before he moved his own arms back up to press against Dean’s chest. 

He closed his eyes, tapping into the Grace within himself and concentrated on Dean and how all he wanted was Dean—for Dean to be happy and for him the understand how important he was. Not only to Cas, but to everyone else as well. 

On Dean’s end of things, he gasped as he felt a rush of energy run through his body, surrounding every inch of him a calming kind of warmth. He felt… protected and safe. As if everyone he cared for was in the room with him, creating a barrier from all the things that hurt inside himself. 

“Cas… What is this?” 

“All of us.” Cas smiled. Slowly—carefully—he pulled his Grace back inside. He opened his eyes to see Dean staring straight ahead at the wall, an expression of real awe and understanding on his face. “Your family.” 

Dean took a moment to collect himself and look down into Cas’s eyes. “What…”

“That's what you mean to us, Dean,” Cas said, moving his hands up to tug lightly at the hair on the back of Dean’s head. “That's what you mean to  _ me.” _ He stood back up on his toes and pulled Dean down to meet him in a kiss. 

It started slow. Dean kept his hands on Cas’s hips until he couldn't anymore and he was picking the boy up and laying him gently down on the bed. He did just as Cas had and kissed every inch of skin he could as clothes were shed. 

Cas kept a tight hold on Dean as they kissed and smiled and whispered  _ I love you _ ’s to each other. Dean kept as close as he could while Cas rolled them over. Cas leaned over Dean, looking into his eyes and smiled before pulling the man to sit up. Dean held onto Cas tightly, pressing his chest to Cas’s; even as the boy grabbed the oil and dripped a fair amount onto his member. 

Cas had a small smile on his face as he positioned himself over Dean, one of his arms thrown around Dean’s shoulders while the other was in the man’s hair. He kept his eyes locked on Dean’s as he lowered himself, letting out a small gasp. 

Dean kept his arms tight around Cas. He pushed his hips up to meet Cas’s movements as best he could. Cas was huffing out small breaths of air as he moved. Both had a warm and tender smile on their face. A smile they would only ever share with the other and never anyone else. A smile they’d never even share with themselves.

Dean and Cas never broke eye contact with each other as they moved. Even when Dean moved his hand up to cup Cas’s face, his thumb resting on the boy’s bottom lip and tugging it down to expose Cas’s teeth before he let go and kissed Cas hard. It took both of their breaths away faster than they thought it would and they had to pull away not long after their lips first touched. 

The look in Cas's eyes had Dean fighting even harder for breath. And the emotion in Dean's made Cas want to melt.  

_ This is different,  _ they thought, _ this isn't like the other times _ . 

Maybe they were both wrong and they were just simply making love; but it felt like more than that. It felt deeper. Maybe they wouldn’t ever be able to explain just why, but that was okay because maybe it really was different. 

Dean was baring  _ himself  _ to Cas and Cas was giving his  _ all  _ to Dean. 

The two of them came apart  _ together _ , absolutely. Just like that, tangled with the other and skin touching skin. Sharing their deepest self with the other, and showing how much they loved the other. 

Cas tightened his grip on Dean as he went over the edge and Dean came at the same time Cas did, with a quiet shout of ‘ _ I love you! _ ’ 

**Notes for the Chapter:**

> Sorry for such a short chapter, guys. Next one should be longer!


	15. Chapter Fifteen

**Summary for the Chapter:**

> Cas gets jealous when he sees some prostitutes rubbing up against Dean in the market. But there's nothing like a night of passion to kill the Green Eyed Monster. 
> 
> The next morning, however, is when the real drama starts.

**Notes for the Chapter:**

> Just a quick thing: I may have fucked up Dean and Cas's ages here, but I'm not certain... I'll go back and edit if I have to, but for now, it is what it is.

Chapter Fifteen

_July 10, 1695_

 

“Judging by the way you’re walking today, I’m guessing you already know Mr. _Hung-like-a-stallion_ is back, then?” Gabe asked, looking Cas up and down once before shaking his head. Cas blushed and looked around to make sure no one heard his uncle. They were in the market on Cas’s day off and like Gabe had said, Cas knew Dean was back. He’d gone and seen him last night.

“Yes,” Cas answered. “Don’t talk so loud, though, Gabe. What if someone were to hear?”

“Oh please.” Gabe waved him off before stopping and looking somewhere off to his left. “Is that… Is that him there?” He pointed to where he was looking. Cas followed Gabe’s finger and sure enough, there was the man himself; standing tall and proud. Benny was next to him and they seemed to be looking over a list. No doubt it was the list of supplies they needed to start stocking up on.

“That’s him,” Cas said, smiling shyly. He quickly picked up something from the table he and Gabe were standing next to — startling the vegetable stand owner — and held it up as if he were examining the item.

“Did you need eggplant for something, Cas?” Gabe asked, a smirk on his face. He shook his head and took the vegetable from Cas, putting it back on the table. Cas blushed again, offering a sorry look to the seller before Gabe pulled him towards Dean.

Cas immediately started to protest. “We can’t be seen with him, Gabe!” He tried to ground himself so Gabe couldn’t pull him any closer but had no luck.

“Don’t be such a baby,” Gabe snorted. “And I’m not that stupid. We’re just getting a little closer, alright?”

“Gabe!” Cas hissed, finally finding his footing and refusing to move another step closer. He darted his eyes over to Dean, immediately stiffening when he saw three women from one of the brothels sidling up to him and touching him. “What do they think they’re doing?”

Gabe looked over and couldn’t stop the cackle that slipped out, “Ha!” He quickly shut up with one look from Cas, though. “Well, they are prostitutes. And Dean is a well known wealthy man. They’re just doing their job.”

“But Dean’s mine—”

Gabe interrupted, “Oh, possessive are we?”

“I am not!” Cas almost hissed.

“Sure,” Gabe laughed. “But anyway, they don’t know that and it’s their job to find wealthy men. If it makes you feel any better, he doesn’t seem to be reacting to it. He seems like he’s ignoring them, Cas.” He shrugged.

“But they’re touching him,” Cas said, his voice low and upset. “They’re touching what isn’t theirs.”

“They are _just_ doing their job, Cas,” Gabe tried to reason.

“He’s not theirs to touch,” Cas seethed. He saw one of the girls press their body right up against Dean’s. Dean shrugged her off, much to Cas’s delight, but the woman was relentless. She just giggled and rubbed her hand over Dean’s chest with a flirtatious smile on her face and pushed her breasts out.

“Again, at least Dean doesn’t seem to be into it,” Gabe said. “And he hasn’t seen you yet.”

“What does that matter?” Cas snapped, finally turning and walking back the way they came. Gabe blew out an exasperated breath, looking over at Dean and catching the man hold up his hand and point to it with a dangerous look directed at the three women. He furrowed his eyebrows when the three women's shoulders tensed and they hastily sashayed up to another man who looked like he had some coin. Gabe mentally shrugged and turned to follow Cas.

“Why are you so upset? Dean wasn’t even interested in them in the slightest,” Gabe asked when he caught up. Cas only shot him a look and shook his head in disbelief.

“You wouldn’t understand,” he mumbled, looking straight ahead as they exited the market and walked along the path back to the Novak Manor. Gabe looked at Cas’s profile, letting out a small laugh.

“I never took you for the jealous kind,” he said, shoving his hands into his coat pockets.

“I’m not jealous,” Cas grumbled, picking up his pace.

“Right,” Gabe said, nodding.

“I’m not jealous,” Cas insisted, his head twitching a little to look at Gabe. “I’m not.”

“I fail to see how this isn’t jealousy.”

“I’m not jealous, Gabe!” Cas raised his voice. “Those… Those…” he searched for a word he could use to express his displeasure towards the courtesans that had the audacity to touch Dean.

“Prostitutes?” Gabe supplied. “Paramours?”

“Whatever!” Cas threw his hands up, “They were touching what isn’t theirs.”

Gabe ‘oohed’ and raised an eyebrow. “You touched that vegetable when it wasn’t yours.”  

“That’s completely different. That was a food item whereas Dean is a human.”

“Okay,” Gabe said, nodding again. “I get it.”

“I don’t think you do,” Cas said, slowing as they came to turn onto the pathway leading to Novak Manor. He walked up to the door, hesitating before opening it. “What do you get?”

“Dean is yours,” Gabe smirked. “And only yours.”

 _“No.”_ Cas opened the door and walked in, not even waiting for his uncle to follow before he headed straight for his room. “He doesn’t belong to anyone.”

Gabe laughed as he followed Cas up the stairs, “Then why are you getting so upset over this?”

“I’m not upset,” Cas rushed out, sitting down on his bed with his back to Gabe and crossing his arms as his uncle flopped down behind him, stretching out over half of the bed.

“What exactly would you call what you’re doing right now then?”

“Not talking to you; for starters. And not listening to you.”

“Oh come on,” Gabe pouted dramatically. “Don’t be rude.”

“Oh,” Cas scoffed, looking at Gabe over his shoulder. _“You’re_ one to talk.”

“I’m not rude.” Gabe moved his hands under his head and closed his eyes. “I’m opinionated.”

“Yeah,” Cas said. “”And you go about stating your opinions very _rudely.”_

“Okay, okay, okay,” Gabe relented. “I’m sorry.”

“You’re not actually sorry,” Cas said.

“Yes, I am!” Gabe insisted, not opening his eyes. “I absolutely am.”

“Right,” Cas said under his breath, rolling his eyes. Gabe sighed exasperatedly and pushed himself up.

“Okay,” he started. “If I help you with your homework will you forgive me?”

“I already finished my homework.”

“Okay… What if I use my ‘magic’ to convince Michael to let you have a few days off with me and you can spend them with Dean?” Gabe suggested, using air quotes around the word _magic._

“Deal.” Cas instantly brightened. _“And_ you actually _can_ help me with my homework.”

“I thought you said you were done?”

“I lied,” Cas said, smiling and shrugging nonchalantly. He stood up and walked over to his desk, grabbing his books and files and papers before coming back and setting them on his bed. “Let’s get to it. I’m seeing Dean tonight and I want to have this done.”

“You sneaky little—”

“Language.”

“For someone who hangs out with pirates, you sure are an old maid.”

“Someone has to be pure on that ship,” Cas joked, smiling as he sorted through his papers. He handed an article to Gabe and told his uncle to read it before checking his answers.

 

~  ~  ~

 

“Does… Does Cas seem weird to you?” Dean asked Charlie quietly, leaning into her personal space as to make sure Cas wouldn’t hear.

“Are you asking if he’s been looking at you without his normal completely smitten lovey-dovey gaze? If so, yes,” Charlie answered. “He seems like he could be upset with you, but I don’t know what it’d be about.”

“Okay…” Dean said slowly, giving Cas a once over before thanking Charlie and walking over to the boy in question. He put his hand on the small of Cas’s back and steered him to a less populated area of the mess.

“Are you okay?” Dean asked, giving Cas a concerned look.

Cas didn’t answer right away. He kept his head down and his hands slowly started to turn into fists as he remembered the women with their hands all over Dean’s chest and pressing their bodies up against Dean. “I’m fine,” he answered curtly.

“Uh… You’re not.” Dean ducked his head to try and catch Cas’s eyes. “Have I done something wrong?”

_“No.”_

“Cas?” Dean asked, surprised by the tone Cas had used. “What’s wrong?”

“I _saw_ you,” Cas said with a stiff jaw. He looked up at Dean and there was a fire in his eyes that made Dean wither a little bit.

“What do you mean?” Dean asked. Cas clenched his jaw and shook his head.

“I saw you today.” He gritted his teeth and then pushed past Dean, making sure not to look back over his shoulder when Dean called his name. When he heard Dean’s footsteps following him, he sped up his pace.

“Cas!” Dean called after the boy as he charged into the cabins hall, no doubt heading for their room together. “Cas, talk to me!” Cas didn’t answer and instead slipped into the captain’s cabin. He waited against the wall, just passed the door, for Dean. “Cas!”

Cas grabbed Dean by the front of his shirt as the man came rushing in and pushed him against the wall roughly. He pressed his body along Dean’s trying to cover as much of the man as he could with his own body. “It’s not enough,” Cas growled in frustration. He fisted Dean’s shirt in his hands and ripped it open before splaying his hands out against Dean’s torso.

“That was one of my favorite shirts,” Dean gasped. He wasn’t exactly sure what to do with his hands and found that he left them hanging at his sides while Cas pushed his shirt to the floor.

“Ahg!” Cas yelled again, “I can still see them pushing up against you, Dean! I can still see them _touching_ you!”

“What?” Dean said breathlessly, “Who?”

“Those… Those… Those _women,”_ Cas spit the word out like he was disgusted it even had to come out of his mouth. “Those prostitutes who thought they could fucking touch you!”

“What about those women? That happens all the time,” Dean said, watching Cas closely as the boy started to unbutton his own shirt. “I just tell them to go away and show them the ring I wear when I’m without you.” Dean held up his left hand and pointed to the silver band. “Sometimes I have to dock at smaller pirate supply stops and the women there — Gods, they don’t leave you alone. So I started wearing this ring and it seems to keep them more at bay.”

“Really?” Cas asked, his face melting and small smile replacing the scowl that he had been wearing. Dean smiled back and opened his mouth to respond but Cas shook his head and the look from before was back. “Th-that's not what I’m angry about,” he said. Dean didn’t have time to respond to what he was angry about before Cas dropped to his knees. He started to furiously undo Dean’s pants, almost as if he couldn’t work fast enough. “I don’t doubt your fidelity, Dean.”

“O-okay,” Dean breathed out as Cas finally was able to pull Dean’s trousers down to about mid-thigh. “What are you angry about then?”

“I’m _angry_ that they were touching you,” Cas said, his voice deep and gravelly. Dean didn’t think that a voice like that could turn him on, but it did and he barely had time to recover from it before Cas’s hands gripped his member tight. “I’m _angry_ they thought they could touch you when you’re not theirs to touch.”

“I made them get off, Cas,” Dean said breathlessly.

“That’s not the point, Dean,” Cas bit out. “The point is that they _had their hands on you._ They put their bodies on yours.” He pumped his hands on Dean’s shaft a few times, making Dean groan quietly before he took the head of Dean’s cock into his mouth.

Dean yelled out in surprise, threading his hand into Cas’s hair. But Cas batted his hand away, looking up at Dean and shaking his head as best he could. Dean tried to respond but found himself letting out a long, low moan as Cas’s tongue worked magic across the underside of his cock.

Cas’s hands pumped steadily in time with the flicks of his tongue. He made sure to set a rhythm that would bring Dean close to the edge without actually making him tip over until Cas wanted him to. The noises Dean was making, scratching his nails and hitting his head against the wall behind him, due to the frustration of not being able to touch, made Cas smile. It was a nice thought that he could reduce Dean to a frustrated mess.

“Cas,” Dean moaned, his head thrown back and his knees bent slightly. “Cas, Cas, Cas.”

Cas pulled off of Dean, his breathing a bit labored as he spoke, “Yes, Dean?” He looked at Dean as if he was the picture of innocence, waiting for a reply and smiling triumphantly when all he got was a groan. “If I make you come now,” Cas paused, turning his head to rub the excess spit off on his shirt sleeve, “Will you be able to go again?”

Dean grunted low in his throat, “Of course,” he said, craning his head down to look at Cas. “For you, anything.” Cas smiled, a slight blush staining his cheeks before he quickly swallowed Dean back into his mouth. Dean’s eyes screwed shut and he groaned out Cas’s name, coming after a handful more pumps of Cas’s hands along his shaft. “Fuck!”

Cas swallowed Dean’s cum, sucking gently for a few beats of his heart before pulling off and standing up. He pushed Dean’s pants down to the floor and Dean immediately kicked them off, allowing himself to be guided to the bed and to be roughly pushed down onto it. Cas told him to sit at the headboard and Dean followed through, watching Cas as he stripped quickly.

“Fuck, man,” Dean mumbled, watching as Cas came to straddle his waist. Cas grabbed Dean’s hand and brought it down to his cock, making the man wrap his hand around the width.  “You’re so fucking hard.” Dean inhaled sharply and let out a huff of a laugh.

Cas thrust into Dean’s hand and growled, “I’m the only one who can get this hard for you.” Dean’s head snapped up to Cas’s and he stared, wide eyed and shocked, at his lover. He felt himself, surprisingly, start to harden again. “You hear me? Only I can get this hard for you. _Me.”_

“Y-yeah,” Dean rasped, not able to tear his eyes away from Cas’s face.

Cas continued. _“_ Only _I_ can make you come as hard as you just did, you hear me, Dean? _Only me.”_

“Only you, Cas,” Dean agreed, tightening his hand around Cas’s cock. “Oh, fuck, _only you.”_

 _“Good,”_ Cas said, nodding in finality. He reached back and lightly gripped Dean’s cock, stroking in time with his thrusts. Dean sat up and nuzzled his face into the crook of Cas’s neck, teething lightly at his shoulder.

“Let me prep you, angel?” He asked, receiving a small nod in response. Dean smirked and quickly cradled Cas to his body before laying the boy down gently, settling himself comfortably between Cas’s legs.

“I didn’t like those women touching you, Dean,” Cas said while Dean found the oil and dipped his fingers in. “I didn’t like having to watch them drape themselves all over you and I could only stand there and watch.” Dean nodded, putting a hand next to Cas’s head to support his weight over the boy while he circled Cas’s entrance with a pad of his finger from the other. “I’m the only one who gets to touch you like that.”

“I didn’t like them touching me either,” Dean whispered, watching Cas’s face with rapt attention. One corner of Dean’s mouth quirked up as Cas’s eyes closed and his mouth fell open when Dean pushed two fingers in. “Still kinda loose from last night, aye, Cas?” He added another finger with no resistance and smiled. “Bet I don’t even need to really prep you, huh?”

“Yes,” Cas moaned in agreement, bending his knees up to open his legs. “Please, Dean, please.”

“Anything for you,” Dean added another finger and rubbed against that special spot that made his boy writhe.

“No, Dean!” Cas whined, throwing his head back. “I want your cock, not your fingers!”

“Gods,” Dean breathed out, feeling his spine tingle. “Okay.”

“Now,” Cas demanded, grabbing onto Dean’s bicep tightly. “Now, Dean!”

“Calm down, Cas, I’m going as fast as I can,” Dean chuckled under his breath, oiling up his manhood as quick as he could and pressing the head of his cock against Cas’s rim. “You ready?”

“Yes!” Cas screamed at him, threading a hand into Dean’s hair and tugging harshly. “Fuck me now!” Dean didn’t wait to obey and immediately pushed into Cas, smiling at the stuttering breath Cas let out.

“Feel good?” Dean asked, a laugh in his voice as he started fucking Cas deep and slow. Cas nodded his head enthusiastically, tugging at Dean’s hair.

“Yes,” Cas moaned; both from the feeling of Dean and in answer to his question. “Harder.”

“You sure?” Dean asked, a sly smile on his face. Cas groaned in frustration and dug the heels of his feet into the back of Dean’s thighs. Dean huffed out a laugh, snapping his hips into Cas roughly, making the boy cry out for more. “Hard enough?” Cas moaned in response, snaking his arm down to gather on his fingers some of the precome that had leaked onto his stomach.

“Feels so good,” Cas moaned, bringing his hand up and pushing his fingers into Dean’s mouth. Dean closed his eyes, moving his tongue between the digits and sucking the taste of Cas off them. There was a sweetness to it that made Dean shudder in appreciation.

When Cas took his fingers out and reached back down, Dean’s eyes followed and his hips stuttered. It looked as though Cas had already come from the pool of liquid on his stomach. Dean was almost certain that Cas had to have come already.

“Did you come without me knowing?” He lifted his eyes back up to see Cas shake his head as he sucked his fingers into his mouth. If Dean hadn’t come before this, he was sure he would have come just from that sight.

Cas darted his tongue out to wet his lips before he pulled his fingers out of his mouth and dipping his hand back down to gather more precum. “Only I can get this wet for you,” he whispered, pushing his fingers back into Dean’s mouth. Dean sucked on them, moaning softly at the pure taste. He didn't know how Cas managed to always taste so good, but he wasn't going to question it. Or complain about it.

Cas pulled his fingers out of Dean’s mouth once more and moved his hand down to grip himself lightly, sliding his thumb over the slit of his cock. Dean craned his head down when Cas didn't bring his hand back up. “Oh, fuck!” His hips stuttered and Dean surged forward to kiss Cas, rough and uncoordinated, thrusting his hips a few more times before he spilled inside Cas with a strangled moan.

“Dean,” Cas moaned against Dean’s mouth, gasping and arching his back as he felt Dean’s cum spill inside him. He went silent as he came, his body seizing up and muscles going stiff. His eyes snapped open wide like the feeling of orgasming surprised him — even after all his time spent with Dean.

Dean groaned Cas’s name as he felt the boy clench around him, milking his cock for all it was worth. Cas gasped for air, riding out the waves of his orgasm with his hand wrapped tightly around his cock and Dean inside him. He felt Dean circle his hips and almost passed out when the pirate massaged the head of his cock into his prostate.

“I got you,” Dean murmured, thrusting his hips very shallowly and smiling at the high pitched sounds Cas let out. “So beautiful, Cas.”

“Dean,” Cas gasped, dragging the hand he had on his cock through the cum and precum on his stomach before he brought it up to Dean’s lips, urging the man to lick it clean. Dean smiled as he darted his tongue out to clean off Cas’s hand. He kept his eyes on Cas’s the whole time, feeling a sense of pride at the dazed look in his lover’s eyes.

When he was done, Dean kissed Cas, slow and tender before pulling out of him and rolling off to lay beside Cas; reveling in the post orgasmic bliss and catching his breath before talking.

“You know… I never took you for the jealous type,” Dean said, shifting onto his side and pulling Cas closer. Cas turned his head to the side to look at Dean.

“I'm not jealous,” Cas replied, his words coming out slower than normal and softer. “I just don't like when people touch what isn't theirs.”

“And I'm yours?” Dean asked, amused.

“Yes… You’re mine and I’m yours.”

“Oh,” Dean drawled, sliding an arm under Cas’s neck for support. “I’m okay with that.”

“Good,” Cas said with finality. “‘Cause honestly you didn't have much of a choice.” He ended his sentence with a yawn before turning on his side and snuggling into Dean.

“You’re tired?” Dean asked, wrapping his arms around Cas.

“Duh,” Cas said sleepily, “I’ve been upset and angry all day. That took a lot out of me.”

“You were angry at me all day?”

“No, I was angry at the courtesans.”

“Ah,” Dean chuckled, smiling. Cas started to giggle, but it turned into a yawn.

“Are _you_ tired?” he asked.

“A little,” Dean responded quietly. He rolled Cas on top of him and then maneuvered them until they were both under the covers.

“Well,” Cas mumbled, pushing his face into Dean’s chest, sighing happily. “We can rest for just a little bit.”

“Just a little bit?” Dean asked. “Why just a little bit?” Cas lifted his head, smiling mischievously.

“Tonight’s gonna be a long night for you, Captain,” he said, giggling as Dean groaned his response.

~~~

_July 16, 1695_

 

“Hey!”

Cas jerked back awake with a start. “Yes! I’m listening.” Gabe cocked his hip and quirked an eyebrow, frowning. It’d been pretty obvious that Cas had not been listening. But it wasn’t entirely his fault. He and Dean had stayed up all night doing some rather… Vigorous activities. Over and over again.

“You do understand that you can’t just put your life on pause while Dean’s here, right?” Gabe walked over to sit next to Cas. “I get that you don’t get to see him much and when you do it’s not for very long, however—”

“Put my life on hold when Dean’s here?” Cas interrupted, looking at Gabe incredulously. “Gabe, I don’t know if you noticed but when Dean isn’t here I am just going through the motions. If anything, when I put my life on hold is when Dean’s not here.”

“When Dean’s here you only pay attention to him,” Gabe tried to reason. “When Dean’s not here you focus more and listen during my lessons. And when he is—” he motioned to Cas’s slouched and tired frame. “—you’re falling asleep or daydreaming about Dean or something else that distracts you. I don’t want you to hate me, but I’m not sure Dean is a healthy influence on you anymore.” Cas took a deep breath, closing his eyes and straightening his back. He opened his eyes, turned to Gabe, looking straight into his eyes, and began speaking.

“I know you’re just trying to look out for me and get me to do what’s best for myself. But uncle, I am not a child. I’m twenty-one and up until I met Dean, I spent my entire life studying, doing as Michael said, and never knowing what _I_ wanted in life. If I hadn’t been late to that meeting the day after I met Dean I’d be married right now. I wouldn’t be who I am now… I’d just be a shell of a human. Because of Dean, I know what I want to do with my life and it's not spending another second more than I have to sitting and listening to other people tell me things.”

“Cas…”

“Once Dean offers to take me with him — once Dean gives me a place in his crew, I’m going with him. I’m leaving with him and I’m not coming back.”

“Castiel—”

“It’s Cas,” Cas stated. “And you can come, too, you know? You don’t have to stay here either.”

“I’m not becoming a pirate,” Gabe said quietly. “I’m not giving up the life I’ve made for myself here on this island.”

“Then I’ll miss you, but I’m not going to change my mind; not for you, not for Michael or my mother, not for anyone. I’m sorry.

“What if I—”

“Even if you told me you were dying I’d still choose to go with Dean.” Cas shook his head and Gabe swallowed a lump in his throat, darting his eyes between Cas’s.

“Why?” he asked. “What’s so special about Dean? The only thing he can give you that I can’t is sex!” Cas’s eyes dampened and his mouth twitched down in the corners. Not in a sad manner. But not in an entirely happy way, either. “It’s not fair because I can’t compete with that! I don’t stand a chance!”

“I don’t care about sex, Gabe.” Cas reached out to grab Gabe’s hand. “He—”

“Then what does he give you that I don’t, Cas!” Gabe yelled. He ripped his hand out of Cas’s and stood up, walking over to the window that overlooked the sea in the town’s library. He glared at Dean’s ship and the moving forms on it. One of them was Dean and right now, Gabe _hated_ Dean. “I don’t get it. Am I not enough for you?”

“No,” Cas answered honestly. “You’re not.” Gabe closed his eyes and fisted his hands at his sides.

“And Dean is?”

“I think you misunderstood me,” Cas said. “You’re not enough reason to make me stay… Gabe, no one is. If you and Dean’s places were switched and he was on this island while you were the one with the ship, my love for him couldn’t make me stay here either.”

“I can tell you thought a lot about this.” Gabe’s voice was bitter.

“I have,” Cas answered. “I wanted to be sure that it was _me_ that wanted to leave and not because it was for anyone.”

“What about Michael? Don’t you want to leave because of him?”

“I want to leave because there’s so much out there that I haven’t seen yet and I _need_ to see it, Gabe. I need to learn firsthand about the world. And I think part of the reason why I want to explore and learn first hand is due to Michael. But even so, I’m glad of how my life’s turned out thus far,” Cas said slowly, bringing his hand up to toy with the gemstone Dean gave him.

“What am I supposed to do when you leave, huh, Cas? What do I do then?” Gabe turned back around, shoving a hand into his pocket and gesturing with the other. “I don’t have anyone but you.”

“You can’t put that on me,” Cas said, frowning. Gabe set Cas with a steely gaze and a firm jaw. Neither of them moved for a whole minute. Cas could see the anger in his uncle’s eyes. But he didn’t feel guilty. No, not one bit. Leaving with Dean was the right decision for his own life. That’s what mattered. Cas needed to look out for himself first and he couldn’t be responsible for the actions of others — to even insinuate that he was, wasn’t fair. “You can’t blame me for your decisions. It’s unfair.”

Before Cas had a chance to react, Gabe was walking over to him and grabbing his jacket. He paused to look Cas directly in the eyes, said, _“Watch me.”_ And then he left; walking swiftly to the stairs and descending them just as quickly. By the time Cas processed what had even happened and looked over to the exit, Gabe was gone.

Cas felt like he’d been punched. Like the wind had been knocked out of him. He’d never seen Gabe so mad. And to know that Gabe was mad at _him_ was even more damaging.

He looked back to the window, opting to stay there for another hour or so until it got dark. After that, he decided he’d go to meet Dean. Although he knew his father would be upset about him not being home for supper that night, he couldn’t find it in himself to care.

 

When the sun finally set and the old woman who owned the library gave him a curious look, Cas left. He kept his the collar of his jacket up, stepping into the alleyway next to the library, watching people come and go for ten minutes and then he stepped out again, heading towards the docks.

Cas stepped onto the Impala, keeping his head down so he wouldn’t get caught with red eyes from crying. He just wanted to find Dean and curl up with him in bed. He was exhausted. Especially considering he hadn’t slept in almost twenty-four hours.

A child’s scream had him shooting his head up and looking in the direction of the noise. He saw Dean catching Ben as the boy fell and then throwing him up again, eliciting another scream from Ben. The happy grin on Dean’s face and the laughing from Ben had Cas forming a smile of his own. Dean was a great man. He was fair and just. Which, unfortunately to some, meant that he had to bend the law.

“Dad!” Ben yelled, laughing loudly and squirming as Dean held him upside down and tickled him. “Dad! Stop!”

Dean laughed, “What? I thought you liked being tickled?” Ben tried to keep a straight face as he responded.

“No! Dad, stop it!” he giggled, failing to keep that straight face. Dean laughed and threw Ben into the air again, catching the boy when he came back down and spinning as he did so. Lisa came by and gave them a look, making Ben look away and Dean nod with a straight face. When she walked away, they both hunched in and talking in hushed tones, giggling every now and then.

Cas felt his stomach squeeze. He wasn’t a jealous person. He really wasn’t, but seeing Dean so happy and at ease… Cas felt a mixture of emotions.

On one hand, he was happy that Dean was happy. Dean deserved so much. He deserved to be happy and be loved and admired. Cas was truly happy that Ben and Lisa had joined him on the Impala because, it didn’t only benefit Lisa and Ben, but Dean, too. All three of them needed the support and love they all gave each other.

But… On the other hand, Cas was sad. He wanted to be apart of that with Dean. He wanted to share that happiness with Dean. It nearly killed him being away from Dean for such long periods of time.

Cas thought about that fact for a moment, asking himself, _that can’t be healthy, can it?_

“What’s wrong?” Benny asked as he came up to stand next to Cas. Cas looked up at him for a second before looking back at Dean.

“Is it bad that when I’m not with Dean I don’t feel alive?” Cas asked. “I miss him so much when he’s gone that I can’t eat or sleep right.”

“I don’t think it’s either bad or good,” Benny said.

“How do you mean?” Cas asked.

“Well… You both need each other. You both give the other something that no one else can or will be able to.” Cas started to deny what Benny said, but stopped short because he was right — Benny was making a good point. Yes, there were other people that Dean could have sex with. But none of them could give them what Cas was giving him. Especially not with where they both were in their lives.

“You’re right,” he said, nodding. The pit in his stomach started to lessen as he saw Lisa finally come over and take Ben from Dean’s arms, pretending to be put out at their antics but smiling as she walked towards the sleeping quarters. She gave Benny and Cas warm smiles as she approached and then said a quiet _‘good night’_ as she and Ben passed.

Benny turned to Cas, giving him a light shoulder squeeze and saying, “I’ve got to go get breakfast ready for tomorrow. I’ll see you later, Cas.”

“Alright,” Cas said absentmindedly as Dean made eye contact with him and his face lit up. “I’ll see you then.” Dean jogged over to Cas, giving Benny a nod before he hugged Cas.

“I missed you,” he said. Cas closed his eyes, hugging Dean tightly and inhaling his scent.

“I missed you, too,” Cas sighed. He buried his face into Dean’s chest, sighing again. Dean kissed the top of his head and pulled back to see Cas’s face. He saw the pinkness of Cas’s nose first, like he’d been wiping and blowing his nose repeatedly. Then he saw the faint traces of tear tracks on his face.

“Have you been crying?” Dean immediately asked, taking Cas’s face in his hands to inspect him. “Baby… What’s wrong?”

“Gabe and I had a fight… He’s _really_ mad at me,” Cas whispered, feeling like he was about to start crying. Gabe had been the only person in the world, when he was a child, that showed him compassion and love.

“I’m sorry, angel,” Dean said, his brow creased in worry and sympathy. “Do you want to talk about it, Cas?”

Cas shook his head softly. “No. Not right now, at least. Can we just go to our room?”

“Of course, baby,” Dean said, offering a smile. Cas felt his knees start to wobble and his bottom lip quiver. He and Gabe had never honestly fought before and Gabe had seemed so angry. Dean bent down and scooped him up. Cas wrapped his arms around Dean’s neck and gave him an appreciative squeeze. He heard Dean hum in response and felt him kiss the top of his head, murmuring a quiet _‘it’s okay, Cas’_ as Dean turned, using his shoulder to open the door to get to their cabin. Shoving his face into Dean’s neck, Cas felt tears ready to fall once they made it to their room.

“He’s never been this mad at me,” Cas whispered. Gabe was the only person he felt loved him for the majority of his life. Up until Dean, he didn’t think that there would be anyone else that truly cared for him except his uncle. He never angered with Cas; even when he did something wrong. Instead, he explained what to do instead and why not to repeat his actions. And he never blamed Cas.

“It’ll be okay, Cas,” Dean said soothingly, finally making it to their room and over to their bed. He laid himself and Cas down, running a soothing hand through Cas’s hair as Cas let himself go and he cried.

“Dean,” Cas sniffled, hiccuping in air.

“Yeah, angel?” Dean said quietly, pressing kisses into Cas’s hairline.

“I just want to forget about what happened with Gabe right now,” Cas whispered. “Will you help me forget?” He tilted his head up to kiss Dean. Dean kissed him back hesitantly, breaking it off a few second after it started.

“Are you sure that’s a good idea?” he asked. “Sex isn’t a solution.”

“Please Dean?” Cas asked. “I know sex isn’t going to solve my fight with Gabe. Hell, if he knew I just came here to talk and sleep with you he’d probably just get more angry with me. But I just… I need to know that even if Gabe cuts me out of his life, o-or he stops loving me or any other multitude of bad outcomes, that you won’t. That you’ll still love me.”

“Cas…” Dean breathed out, looking at Cas with wide eyes. He cupped Cas’s face and kissed his forehead. “I’m not going to stop loving you.”

“How can you be sure?” Cas said. “Emotions are fickle and they can change in a day. You could wake up tomorrow and I could say something and then, bam, you hate me. Or two years from now we could start drifting apart and then one day… Bam,” Cas looked away, his eyes welling up with yet even more tears. “You don’t love me anymore and all those quirks that you used to love about me you now hate them and they drive you insane. How can you be so sure that you’re not going to stop loving me?” Dean didn’t even hesitate to respond.

“Because I’m committed to you. I want to find the best in you even on your worst days. I’m loyal to you, and I want to work through any and all problems we have in the future,” Dean said. “And because I love you, I’m not going to have sex with you.” Cas buried his face in Dean’s chest. “But because I love you, we’re going to lay here, I’m going to spoon you and hold you while I tell you all the things I love about you.” Dean gave Cas a squeeze. “How does that sound?”

“I love you, Dean,” Cas whispered, shifting to face away from Dean. “I really love you.”

“I love you too, Cas,” Dean responded, sliding his arms around Cas’s middle and pulling him back against his chest. “Now close your eyes and relax. I know you’re tired, so I’ll talk to you until you fall asleep.”

“Thank you, Dean,” Cas mumbled, burrowing back into Dean’s chest.

“You’re welcome, baby,” Dean said softly, kissing Cas’s temple.

~  ~  ~

_July 31, 1695_

 

Cas woke up to darkness. Usually, even in the wee hours of the morning, he was able to see a little bit. The moonlight always provided more than enough light to see when it would filter in through the window in the cabin. But now he couldn’t see anything. There was something blocking his vision.

“Dean?” he asked, sleep still evident in his voice. He tried to stretch himself out, aiming to pull whatever was over his eyes off, but he found that he couldn’t move. “What?” He tried to remember what happened last night. All he came up with was him and Dean falling asleep, face-to-face while laughing and whispering jokes to each other. “Dean?” Cas pulled at the restraints around his arms again. He tried to move his legs and found that they were also tied up — just like how Dean had tied him up when he wore those panties and Dean put the cockring on him.

“I’m right here,” Dean whispered. Cas finally registered Dean’s warmth on top of him and relaxed into it.

“What are you doing?” he asked, “You have to leave in the morning.”

“I do. I have to leave in about five hours,” Dean responded.

“So why are we awake now?” Cas retorted. Dean chuckled, kissing Cas’s forehead.

“Sex...” Dean started, smirking at the little gasp that Cas let out. “...seemed like a good idea?” Cas’s breath caught in his throat, preventing him from answering. “Although,” Dean started, moving away from Cas and pulling the blindfold up just a bit to give Cas a peek at him. “If you don’t want to—”

“No!” Cas gasped, trying to rock up into Dean. He felt the faintest brush of skin on skin and that’s when he noticed that he and Dean were naked. “Please, I want to.”

“Okay,” Dean said, smirking and letting go of the corner of the blindfold. Cas’s vision was back to complete darkness. “Well… What do you want me to do?”

“You didn’t have something planned out?” Cas asked. He could feel Dean hovering just above him, but he wouldn’t touch.

“Of course I have something planned out,” Dean chuckled. “But I want to know if there’s anything specific you want.”

“Not that I can think of at the moment,” Cas responded breathily. “I just want you to touch me.”

“Hmm,” Dean murmured. “Okay.” He immediately dived down and took one of Cas’s nipples into his mouth, sucking gently and flicking his tongue across the little nub.

“Dean!” Cas gasped, arching into the sensation. Dean thumbed over Cas’s other nipple a few times, getting it hard before he rolled it between his fingers. He pinched and pulled at the bud, reveling in the little gasps and whimpers that Cas was letting out.

“I should play with your nipples more often,” Dean said, his breath ghosting over Cas’s skin. “I love the noises you make when I do.”

“They’re different — ah! — noises than usual?” Cas asked, jerking against the bed when Dean bit down lightly, just to warm Cas up before biting down harder. He stopped just short of when it would be too painful and used the pad of his finger to massage away any residual hurt. It stung a little. But it stung in just the right way.

“Only slightly,” Dean mumbled, moving his finger away and flicking his tongue out against the reddened bump. “You’re higher pitched and it’s both one of the cutest things ever and one of the hottest things ever.”

“Really?” Cas asked.

“Oh yeah,” Dean said, kissing the skin around Cas’s nipple before moving across his chest to his other nipple and repeating everything he did to the first to the second. “Fuck, you’re so beautiful, Cas.” He licked his way down to Cas’s hips, peppering the skin with small kisses as he continued to pinch and pull at Cas’s nipples. There was no doubt in his mind that the red little buds were almost painful to the touch.

“D-Dean!” Cas gasped. He was almost completely out of it and entirely focused on Dean’s mouth on his hip bones and his fingers pinching and pulling oversensitive nipples.

“I know, baby,” Dean said, a light and airy tone to his voice. He used both his hands to pinch Cas’s nipples as he kissed down to the boy’s hip bones. “I got you.”

“N-no,” Cas gasped. He could feel the familiar feeling of heat pooling in his belly and wanted to warn Dean he was about to come but he couldn’t get the words out. All he could do was pant and moan as Dean continued his assault on his chest. “Dean! Dean, I’m — _Dean!”_ Cas came then. Moaning loud and high in his throat as the pleasure coursed through him. He could feel Dean still playing with his nipples and it only added to his pleasure.

“Cas?” Dean’s voice was muted for the moment. Just as he rode the highest wave of pleasure before he came drifting down with the gentle massages of Dean’s fingers on his nipples helping him.

“Dean,” Cas whimpered and Dean got the message. He stopped touching the unbelievably red little nubs on Cas’s chest.

“Cas?” Dean said again. The next thing Cas knew, Dean was pulling off the blindfold and looking down at him in wonder. It took Cas a moment to register that the lines of white on Dean’s face was cum. And it took him another moment to register that it was _his_ cum.

“Oh, my god, Dean,” he gasped, eyes wide and heart pounding. “I—” Cas choked, a blush coming to his face. “I’m sorry. I tried to get the words out to tell you I was going to come, but—”

“You just came from nothing but having your nipples played with.”

“I—”

“You just came from nothing but having your nipples played with!” Dean breathed out again. He looked between Cas’s eyes wildly; searching for something. “Did you know you could do that?”

“N-no,” Cas stuttered.

“Oh, my gods,” Dean whispered. He closed his eyes, taking a deep breath before opening them. A hint of a smile came onto his face. “Okay, new plan. I—”

“Dean,” Cas interrupted. “You know you have…” he darted his eyes over the cum on Dean’s face. “You have m-my cum on your face.” Dean’s eyes widened then and he scrambled to open his nightstand. He pulled out a small mirror after a few seconds and held it up to look at himself. Cas held his breath while Dean looked at himself.

“Fuck,” Dean gasped. “I never thought I’d like seeing someone else's cum on my face...” He collected all the cum on his fingers, wiping it off on the bed before he dropped the mirror.

“Dean?”

“Oh, fuck,” Dean breathed out, shifting so that he sat back on his heels with his thighs flush against the back of Cas’s and his knees up bracketing Cas’s hips. His hands came to curl around the boy’s ribs while he dropped his head onto Cas’s chest. “Jesus,” Dean whispered, sounding a little pained. His breathing started to speed up and Cas started to worry.

“Are you okay?” Cas asked. Dean dug his fingers into Cas’s ribs lightly as he inhaled shakily. “Dean, look at me, please?” Cas canted his hips up a little to get Dean’s attention.

“I’m okay,” Dean said, lifting his head. He had a smile on his face as he straightened his spine. “I’m just processing everything.”

“What were your processing?” Cas asked, looking into Dean’s eyes.

“I just was thinking that cum — _your_ cum on my face wasn’t such a bad thing to see,” Dean said. “I used to hate the thought of someone else's cum on me… But yours?” He dipped down to place a chaste kiss to Cas’s lips. “One word: _hot.”_

“Really?” Cas asked breathlessly.

“Oh, yeah,” Dean said. Cas smiled back at him, tugging at the cuffs around his wrists.

“Will you untie me so I can touch you, now?” he asked. His breathing hiccuped as Dean’s pupils dilated and lust flashed through his eyes.

“I’m not finished with you, angel,” Dean said. “I wanna see how many ways I can make you come without touching your cock.” Cas’s eyes widened.

“What?”

“We already know you can come from my cock and my fingers, and I can probably make you come from my tongue...” Dean paused, giving Cas a smug-satisfied look. “But I should probably make sure I can do that, shouldn’t I?” Cas breathed hard, watching Dean closely as the man reached for a strip of cloth Cas assumed to be the blindfold. “I want you to have to focus on the sensations,” Dean explained, situating the blindfold over Cas’s eyes and tying it around his head securely. “Can you see anything?”

“No.”

“Good,” Dean mumbled. Cas felt him move on the bed and the next thing he knew Dean’s stubble was scratching the insides of his thighs and his breath was making goosebumps rise on his skin. “Do you think you’d be able to come from just my voice?” he asked. “Dirty talk?”

“M-may-maybe,” Cas whimpered. Dean chuckled as he grabbed a pillow, that wasn’t being used and situated it under Cas’s hips

“Oh, baby,” Dean cooed, rubbing his thumb over Cas’s perineum and watching Cas’s pink hole tighten in anticipation. He moaned in appreciation at the sight, wetting his lips before diving in, flicking his tongue across the muscle few times. The surprised noises Cas let out were music to Dean’s ears. He slid his hands up the insides of Cas’s thighs, making his way to grip the boy’s hips. “I’ll have to try to make you come from just talking after this,” he said, smiling at the desperate whine Cas let out. “Explaining to you what I want to do to you?”

Dean went back to eating Cas out, circling his tongue around Cas’s rim before he used the grip he had on Cas’s hips to pull the boy towards him as he drove his tongue forward.

“Dean!” Cas cried out, clenching down on Dean’s tongue.

“Hm,” Dean hummed, smiling to himself. Cas wasn’t hard to work up. You just had to know which buttons to push, and Dean knew the _exact_ ones to push. And he knew when to push them.

Dean shoved his tongue into Cas, massaging his inner walls until he started whimpering. From where his arms were, Dean could feel Cas’s thighs trembling and he pulled away as he brought his hand down to rub his finger over Cas’s rim.

“Yes,” Cas gasped, “Inside… Please, Dean… Please?”

“Not now,” Dean said, experimentally dragging his nail gently over Cas’s rim to see what noise he could pull from Cas.

“Dean!” Cas _screamed_ , convulsing into himself, as much as he could with the restraints around him, and came in thick ropes over his taut stomach and chest.

“Fucking hell,” Dean gasped, pushing himself up to look at Cas and watching as he relaxed before curling forward into himself. “My gods…”

“Touch me,” Cas gasped. “Touch me, please!” Dean obliged him, smoothing his hands over Cas’s sides and the tops of his thighs. Cas cried out, moaning wildly and uncontrollably. Like every nerve in Cas’s body was on fire and when Dean touched him, the fire was doused.

“Cas?” Dean whispered, sliding his hand up to remove Cas’s blindfold. He was met with fluttering eyelids and glazed over eyes. “Baby?”

“Everything—” Cas moaned again, arching into Dean’s hand. “—so good!” He snapped his eyes open, meeting Dean’s and silently begging for a kiss. Something Dean gave him willingly, not hesitating to slide his tongue into Cas’s mouth to gently help him to come down from his orgasm. Cas yelped, curling forward and breaking the kiss. “Please?” he whimpered, shaking so hard Dean could feel it in his own bones. Dean nuzzled into Cas’s neck, kissing his skin softly. He could tell that Cas was about at his breaking point and he reached up to start tugging at the knot that kept Cas bound. “Please? I can’t t-take much m-more.”

“Of course, baby,” Dean whispered.

“I’m sorry,” Cas whimpered.

“No, baby,” Dean whispered, kissing Cas’s neck tenderly before lifting his head to smile down at Cas. “No, don’t be sorry. You’ve done so well, Cas. You did so perfectly and you didn’t even have to try. Okay? You’ve impressed me so much, already, baby. Don’t be sorry.”

“Okay,” Cas whispered, closing his eyes and nodding his head.

“Alright, Cas, what do you want me to do? You want me to untie you?”

“Yeah,” Cas said, his voice coming out barely above a whisper. “Wanna hold you.”

“You got it, baby,” Dean whispered back, giving one last tug to the rope before it fell undone quickly and Cas’s arms curled around Dean instinctively, his fingers digging into the muscle on the man’s back.  “Now what would you like?” Dean nuzzled back into Cas’s neck.

“In-inside,” Cas gasped, shivering as Dean’s breath tickled his neck. “Inside me.”

“You want my cock inside you, angel?” Dean asked.

“Yes, Dean, please?” he whimpered, feeling the restraints around his legs go slack, too, and as Dean reached for the oil, Cas wrapped his legs around Dean’s waist. “Everything felt so good… Everything still feels so good.”

“Tell me about it,” Dean asked softly, expertly uncapping the oil and dipping his fingers in before he brought his hand back to Cas’s entrance.

“Feel like I’m still coming,” Cas gasped out, crying out softly as Dean pushed a finger into him. “My whole body feels like it's just nerves.”

“Yeah?” Dean asked, adding a second finger.

“Yes,” Cas moaned, throwing his head back and clenching down on and around Dean. “Please, Dean?”

“I got you, baby,” Dean whispered, pressing Cas down into the mattress with his body.

“Please,” Cas sighed, threading a hand into Dean’s hair. “Please?”

“I know,” Dean cooed, lifting his head to give Cas small kisses as he quickly worked him open. “Almost there.”

“Please be inside me,” Cas sobbed, digging his fingers into Dean’s shoulder and crying out as Dean brushed past his prostate. _“Please,_ I need you inside me.”

“Okay,” Dean agreed, making quick work of oiling up his manhood and pushing in right away. Cas sobbed, letting his head fall back onto his pillow. “I love you, Cas,” Dean whispered. “You’re perfect, my angel.”

“Dean,” Cas whimpered. Dean rocked his hips into Cas, pulling out not even an inch each time before pushing back into Cas. “I love you, I love you, I love you…” Cas repeated himself like a prayer, clinging tight to Dean in every possible way.

“I know, baby,” Dean cooed, “Me too. I love you, too.” Dean grunted, pushing flush against Cas and coming buried deep inside him. “Fuck, Cas.”

“Yes,” Cas sighed, making a choked off gasping sound in the back of his throat. He relaxed his limbs and melted into Dean’s warmth. “So good.” Dean slowly lifted his head and placed a sloppy kiss to Cas’s lips, smiling down at him when he pulled back.

“I love you,” he whispered, rolling them onto their sides.

“I love you, too,” Cas said, closing his eyes as a soft sated smile spread across his face.

~  ~  ~

“Do you always have to go so early in the morning?” Cas asked, twisting around from where he was, between Dean’s legs with his back to the man’s chest, so he could feed Dean an apple slice.

“It's either early in the morning or late at night,” Dean said, happily chewing the apple in his mouth. Cas made a small disgruntled noise in the back of his throat.

“I don’t like not waking up next to you,” he mumbled, opening his mouth to let Dean put a piece of chocolate into it. “I want to wake up next to you every morning.” Cas lifted his arm again, giving Dean an apple slice and a piece of cheese. “I’m sorry for bringing this up right now… But I need to know; when are you going to take me with you?” Dean chewed slowly, taking his time to answer before he swallowed.

“Cas—”

“I know you said that when the time was right you’d take me with you,” Cas interrupted. “But I know you, Dean. The time is never going to be right for you… You know I’m right.” Dean looked between Cas’s eyes, searching. “Give me a date? I can’t keep this up. I need to know when I can finally start living my own life.”

“I…” Dean took a deep breath after he swallowed. “Twenty-five,” he said. “When you turn twenty-five, I’ll take you with me.”

“That’s four years from now, Dean.” Cas took Dean’s hand in his, shaking his head. “I can’t wait that long.”

“Why not?” Dean sounded like a child asking that. “It gives you plenty of time to really consider your options.”

“I’ve already considered my options,” Cas whispered, placing a kiss on the back of Dean’s hand. “I know you’re scared that I’m going to change my mind or regret coming with you. But I promise you I’m not going to.”

“You don’t know that.”

“I do,” Cas said, lacing his fingers between Dean’s. “I know I’m not going to regret coming with you as sure as I know that I love you.” Dean closed his eyes taking a deep breath.

“Twenty-four?” he asked, his voice quieter than Cas had ever heard it.

“No,” Cas said, turning his head to kiss Dean’s cheek.

“Twenty-three,” Dean said.

“You’re getting closer.”

“Cas,” Dean pleaded.

“Dean,” Cas shot back. Both were silent after that.

Cas gave Dean the time he needed and Dean tried to keep himself from dwelling on the possibility that Cas could change his mind at any time in the future. It was an almost crippling thought.

“I can’t,” Dean announced, giving Cas’s hands a squeeze.

Cas started, sighing a little bit, “Dean, that’s—” 

“I don’t want you to wake up ten years from now and regret giving up your life for me,” Dean whispered. He closed his eyes when Cas twisted himself around to face him. Cas’s thighs rested over his own and he took comfort in the weight.

“Dean?” Cas started, “I’ve said this before, and I meant it then just as much as I mean it now: You deserve to get what you want. And I know that I’m what you want; or at least something you want.”

“You’re _all_ I want,” Dean whispered, making Cas smile at him.

“Then stop denying yourself,” Cas said. “I know you’re worried that I’m going to regret coming with you, but I can promise you that I’m not. Part of the reason that Gabe and I got into that fight was due to that he didn’t want me to leave with you.” Dean opened his mouth to speak, but Cas gave him a look as he continued. “He thought I was leaving because I wanted to be with you. Which, I’ll admit, is going to be a big perk. But it’s not the reason I want to leave.”

“Really?” Dean asked, opening his eyes to look at Cas. He found himself smiling a little at Cas’s confession. If Cas didn’t want to leave because of him… That was… Great.

“Really.” Cas kissed Dean’s forehead, smiling back at him as he continued. “I want to leave because I want to explore and see the world. I want to learn what it has to offer. Like I told my uncle if your and his positions were switched, not even my love for you could stop me from going with him.” Dean smiled.

“When did you get so grown up?” he joked. Cas smiled wider, shrugging his shoulders as he answered.

“Somewhere in between all the sex.” Dean slid his hands around Cas’s waist, laughing as he leaned in to kiss him. He rested his forehead against Cas’s after he pulled away, smiling to himself. Cas brought a hand up to run through his hair. “You’re not upset with what I said, are you?”

“What do you mean?” Dean asked, pulling away enough to look into Cas’s eyes. “What would I be upset with?”

“When I said that if your and Gabe’s positions were switched,” Cas started. “Not even my love for you could make me stay.”

“Absolutely not,” Dean said, a tone of finality in his words. “Cas, there’s you. And there’s me. And then there’s you and me. I don’t want you and me to overshadow _you._ Just because we’re in a relationship doesn’t mean that I want _you_ and what _you_ want to disappear just because we’re together.”

Cas smiled, saying, “Me too.” He cupped Dean’s face. “I don’t want you to disappear into our relationship either.”

“Right,” Dean replied. “But, between you and me…” He leaned forward like he was about to share some deep secret with Cas. “I do like being us more than I like being just me. I know who I am outside of us; I just prefer the me I am when I’m with you.” Cas smiled shyly at him, nodding his agreement.

“I love you,” he said, pressing a quick kiss to Dean’s lips.

“I love you, too,” Dean said. Cas twirled his fingers into the hair just behind Dean’s ear, chewing on his bottom lip a little before speaking again.

“You never gave me an answer.”

“Right,” Dean breathed out. He took a moment to breathe in and then out in an attempt to ground himself. “What about… I… Thirty.”

 _“Dean,_ that’s—”

“When _I_ turn thirty,” Dean clarified. “Next year… I’ll come back for you around my birthday and I’ll take you with me.”

“Really?” Cas asked, beaming at Dean with a big, blinding grin on his face. Dean loved that smile.

“Really,” he confirmed. Cas pulled him down to crush their lips together, slipping his tongue into Dean’s mouth and coaxing it into his own. He moaned as Dean got the hint and massaged his tongue, gently pushing him to lie back on the bed. A little thrill jumped through him when Dean did something with his tongue that could only be described as _heavenly._

“You know,” Cas panted, gripping Dean’s shirt collar as Dean’s tongue trailed along his neck. “If I wasn’t so tired from earlier I’d want to fuck again.”

“Oh, yeah?” Dean asked, a happy tilt to his voice.

“Definitely.” Cas hummed happily as Dean mouthed over his neck, placing small kisses here and there.

“I guess we’ll just have to take a rain check, then,” Dean said, burying his face in Cas’s neck for a moment before pushing himself up onto his hands and searching for their plate of food. He grabbed a piece of chocolate and put it in his mouth, smirking down at Cas as he dived back down to kiss him. Cas moaned softly, eagerly accepting Dean’s chocolate covered tongue into his mouth.

It didn’t take long before they had to pull away; both were panting into each other’s mouths too much for any kissing to continue. When Dean pulled away, a laugh escaped from his mouth. There was chocolate smeared around Cas’s mouth. And judging by the smile and amused look in Cas’s eyes there was no doubt in his mind that his face looked the same.

“You’ve got a little something on your face,” Cas giggled, untangling a hand from Dean’s hair and bringing it to wipe off the chocolate from his face. Dean smiled as he did the same, licking the chocolate off his fingers after he was done.

They stared at each other for a moment, bathing in the affections of the other. But that moment ended much too soon for their liking. It was interrupted by Dean’s alarm going off. Alerting them both that they needed to get going.

“Damn,” Dean sighed.

“We need to clean up and I need to get back…” Cas said quietly, frowning as he turned to look at the alarm. “You have to leave in an hour.”

“Fuck,” Dean groaned, burying his face in Cas’s neck. “Mhm… I don't wanna go.”

“I don't want you to go either,” Cas said. “But you have to go kill some bastards.” Dean only huffed in response, not making a move to get up. He just pushed his face into Cas’s neck further. “Dean, c’mon.”

“No,” Dean mumbled. Cas smiled at his antics, pushing at his shoulders to get him to move.

“The sooner you leave, the sooner you can come back, Dean,” Cas reasoned, using his old line from way back when.

Dean groaned in defeat, giving Cas’s neck a quick kiss before hauling himself up and off Cas. “Fine. You make a good point,” Dean huffed, sitting back on his heels. “An annoying point, but a good one,” he added as an afterthought. Cas pushed himself up onto his elbows, smiling and giggling softly at Dean.

“Everything is annoying to you when you have to do something you don’t want to,” Cas said. Dean nodded, placing a quick kiss on Cas’s forehead before he sprang into action. He got off the bed, helping Cas up, too, before walking over to his dresser and pulling out clean clothes for himself and Cas.

They each got dressed quickly and then left the Impala just as quickly, walking slowly on the path they took to get Cas home. The silence between them as they did walk was promising. Dean held Cas close, and Cas held Dean tightly.

When they reached the spot Dean was to drop Cas off, they shared quick kisses and then Cas parted, giving Dean soft and comforting smile as he said _'I love you'_   one last time.

**Notes for the Chapter:**

> I hoped you liked this chapter!
> 
> I did some chapter outlining and planning and I've discovered that there are about five chapters left for this story until it's done. Five minimum, eight maximum, most likely. And I've got more free time now so I'll be able to write more. :) I'm hoping to get the next chapter up by next week. 
> 
> Till next time!


	16. Chapter 16

**Notes for the Chapter:**

> So, so, so sorry this has taken so long to write! A lot came up all at once and then I got in a car accident and that really skewed my life out of control. (Thankfully everyone was okay; just some sprains and bruises. I got the worst injuries out of everyone in the car, unfortunately, and I'm still recovering from them.) 
> 
> I have an announcement for all of you reading my fic at the end. Nothing bad or anything to be worried about. It's good news, in my opinion. 
> 
> Anyway! I'm writing the next chapter as you actually read this, and it'll probably be up pretty soon 'cause it's gonna be a short chapter; but, just an update to where the ending to this fic is gonna be: three more chapters, and then an epilogue. So, we're nearing the homestretch. 
> 
> NOTE: This chapter isn't edited, so, excuse any mistakes or any awkward places in this chapter, please. :)
> 
> That's all I have to say before this chapter. I hope you like it and the next chapter will be up within the next week.

_ September 17, 1695 _

 

Dean sat at his desk finishing up the paperwork for his last deal when he realized the time.  _ 11:42 PM. _ He pushed himself out of his chair, looking over at his bed. Lisa and Ben were sleeping under the covers. It wasn’t a normal occurrence. Their room was across in the hall—the one Dean and his crew used to store their most expensive goods. It’d been converted to a cabin for Lisa and Ben not too long ago when Dean had had enough of the Braedens sleeping below deck with the rest of his crew. Dean wanted them to be close, but also to have their own space. 

Anyway, today was different. It’d been one of  _ those _ days for Ben. He woke up on the wrong side of the bed. All day, he’d been following Lisa or Dean around and moping about nothing and everything. He didn’t stop whining until one of them picked him up and if they tried to hand him off to someone else he just started crying. 

It was a trying day. They’d gotten through it, though, and gotten Ben to bed. Lisa fell asleep soon after and that’s when Dean carefully extricated himself and started working. For the past two hours he had been sitting behind his desk reading carefully through his work and making any last minute changes he saw fit. At this moment, however, Dean was tired and he was ready for this day to end. 

He quietly walked out of his cabin, making his way to the room across his and entering. It had taken a bit of doing, but Kevin and Ash had been able to get a bathroom installed. Lisa had almost talked him out of doing it, saying,  _ “You’ve already given us so much, we don’t need a private bathroom when there are the ones below deck.” _ Dean had almost listened to her. Now, though, he was so glad he hadn’t. For more reasons than 

Dean pulled off his shirt, dropping it to the ground as he entered the bathroom and turned the water on. After waiting a bit for the water to warm up, he quickly shed the rest of his clothes and stepped in, sighing as the hot water poured over his body. The mental image of the water washing away his troubles of his day and running into the drain soothed him. A small victory for today, if anything. Even if it was just a thought. 

When Dean stepped out of the shower, smelling like Lisa’s perfume infused soaps, he grabbed a towel to wrap around his waist before walking out and checking the time again: 11:58. 

_ Good, _ he thought, walking over to the door and locking it. He didn’t want any interruptions while he was doing this. 

After locking the door, Dean walked back to the bed, dropping his towel as he walked, and laid down. He checked the time again and put a hand on his stomach. The other hand he placed behind his head just as the clock struck 11:59. He gave it a second before he closed his eyes and let his thoughts wander to Cas. 

There was nowhere he’d rather be than with Cas’s right now. Less than sixty seconds from right now would mark the third anniversary of when he first saw Cas. When he met Cas, and when he took Cas’s virginity. Even now, three years later, the kid was still just as breathtaking than the first time he saw him. He was probably even more so, if Dean were being square. There was nothing Dean wouldn’t do for that boy. Absolutely nothing. 

It was almost ironic how a small kid from a small town had  _ The Pirate King _ wrapped around his little finger. Every single little thing about Cas was perfect and amazing and Dean believed, down to his very core, that Cas deserved anything and everything he wanted. 

If he asked for gold, Dean would gladly give him all he had. If Cas asked for rare jewels or priceless artifacts or expensive clothes made from the finest silk? Dean would make damn sure to get him the  _ rarest _ jewels, he would steal  _ every _ artifact in the world, and he would  _ hand weave _ each article of clothing to give to Cas. 

_ His _ Cas, with his raven hair that seemed to always be styled in a manner of bed head. Those bluer than blue eyes that Dean was certain held entire galaxies in them. His lips that were the absolute best shade of pink and were plump and perfect. His shoulders and waist and hips—oh, those  _ hips. _

The same hips that seemed to be on permanent standby until Dean’s were pressed against them. They cradled Dean’s every time they met and just about called out to Dean, begging to be smothered by his own. Just like Cas called out to Dean whenever they were in the same room. Hell, whenever they were in the same fucking city. 

Dean called out to Cas, too. Just as much; maybe even more. 

The clock on the night table beeped—

 

_ September 18, 1695 _

 

—alerting whoever may be in the room it was midnight and that it was the eighteenth. 

Dean breathed out, smiling as his thoughts ran rampant about Cas. All the things they had already done together and all the things they still yet to do. He thought about their first night together. The way Cas had looked at him like he’d been shown a new world. Which in a way was true. In another way, Cas had shown Dean a new world, too. A better world. 

Dean let himself drift into having less than pure thoughts about Cas. About all the ways he could make Cas come undone, the noise Cas made just after he bottomed out inside him, and about how beautiful Cas always looked after sex. 

Dean imagined that he was with Cas, kissing his lips languidly. Like they weren’t in any rush and had all the time in the world—or rather, there was no such thing as time. He imagined that Cas was spread out beneath him, looking up with love and adoration in his eyes. That was something that Dean could never get tired of: the way Cas looked at him. He would never get over how amazing it felt that he was the one Cas shared himself with. Cas made Dean feel like a God. Or like he was flying. 

Cas didn’t have to do much to make Dean feel good, though; but he was always so eager to try new things to please Dean, anyway. It warmed Dean’s heart and made him love Cas even more. A feat he thought impossible. Cas always had a way of showing Dean a new depth to something he’d thought he’d already explored, though. 

Himself, for example. Dean knew that he was damaged. And he  _ thought  _ he’d accepted that that was just going to have that be a part of who he was for the rest of his life…but then Cas had come along and changed everything. Cas helped him to  _ finally _ see that his past wasn’t  _ him. _ It was a part of him, sure, but it wasn’t his identity. And, yes, others had told him the same. It just took someone as pure as Cas to show him that he meant it. That everyone meant it. And just how much they  _ all  _ meant it.

Dean brought himself out of his head as he ran his thumb over the slit of his cock.  An image of Cas with his mouth open in a perfect little  _ ‘o’, _ looking up at him with hooded eyes flashed behind his eyelids. 

“Fuck,” Dean hissed as pleasure ran through him. He slid his hand along the length of his cock slowly, imagining that it was Cas that was touching him.  

Sometimes it worried him how much of his relationship with Cas was based on sex. For him, it was never just sex. Not ever. Sharing that part of himself with someone meant something more to him than it did to a lot of people. 

However, he also knew that not everyone worked the way he did, and he didn’t want to make it seem as though sex was all he cared about. He’d brought the conversation up with Cas one day when he was having doubts, and it seemed like it was the first time Cas had ever even considered that thought. Cas just said that he never thought of them having sex as just sex. Each time they were together he’d always thought of it as…well, as an act of love and closeness between them. Dean agreed; very much so. He’d never thought of his time with Cas as just sex. But sometimes...sometimes he needed a reminder that Cas felt the same way. 

_ “Cas,” _ Dean moaned quietly, running a hand through his hair and moving his other hand faster over his manhood. He thought of the time he’d made Cas come four times back to back just by whispering dirty things into his ear and massaging his fingers against Cas’s prostate. That boy was honest to Gods the single most sensitive person he’d ever met. It was unreal how sensitive Cas was. Dean knew a lot about sex. He knew where humans held pleasure spots and how responsive each spot could be, but Cas was showing him new extremes. And Dean  _ loved _ it. He loved every second that he could give Cas the pleasure and love he deserved. 

Back on that fateful day when Dean first saw Cas, something in him snapped. He was drawn to the boy stumbling across the ports’ quad and he wasn’t entirely certain why…perhaps it had something to do with just how much Cas was calling out—seemingly to the heavens—for someone to love him. And with so many years of no one—not God or angels or whoever may or may not be up there—answering? Cas’s longing began to just seep out of him. From every pore in his skin he oozed of the want to belong. It reached out to Dean—to his own want to have someone love him, too. They were both reaching out for something or someone in the dark. And in that reaching they caught each other. That was a miracle and a blessing if Dean had ever seen one. 

The bond he and Cas had was once in a lifetime—one in a million. Not only did he see it, but so did everyone around him. Garth had even pulled him aside and congratulated him on reeling in someone like Cas. For fucks sake, Ben had asked him once why  _ Papa  _ wasn’t coming with them. It took everything in Dean not to turn the ship around, then. 

Dean shook his head to clear it, replacing his thoughts with solely Cas. Thinking of anything other than him would defeat the purpose of being alone at the moment.

He imagined Cas beneath him, panting and begging for more. More of  _ him. _ More of his touches: his hands here, his fingers there, his tongue inside, his mouth on  _ something. _

_ “Cas,” _ Dean groaned, his breathing starting to pick up as he felt heat coil low in his abdomen. He could almost hear Cas’s voice now. 

_ “Dean, please. Please? Want us to come together.” _

“Fuck!” More images of Cas darted behind his eyelids…

Cas lying on his back, on the edge of their bed, with his thighs trembling around Dean’s head as he was eaten out and stroked until he was coming all over himself...

...Cas on his knees with his back to Dean’s chest, gasping for air as he came hard enough that cum hit his chin...

...Cas sprawled out on their bed with baby blue silk and lace panties that he definitely got from Jo...

...Cas in his lap, clinging to the fabric on his shoulders as he rocked their hips together. 

Dean thought of everything Cas and before he knew it he was coming with a sharp inhale and a jerk of his hips. 

He cleaned himself up after that, wrapping a clean towel around his hips before climbing under the covers and turning onto his side. Exhaustion finally settled into his conscious and he closed his eyes, thinking of how Cas always had some kind of glow just after an orgasm and how beautiful it made him look.

With that thought in his mind, he fell asleep quickly; a small smile on his face. 

 

~  ~  ~

 

_ October 29, 1695 _

 

“Castiel.” Cas felt someone’s hand on his shoulder, shaking him awake. “Castiel.” He blinked his eyes open to see his father standing there above him, a giant grin on his face. “Castiel, pack your bags. You’ll need a week’s worth of clothes. Hurry.”

“What?” Cas pushed himself up as his father turned away from him. “Father, what are you talking about?” Michael opened his closet door in a flourish, looking at all the shelves and hanging clothes. 

“Where do you keep your bag, Castiel?” he asked. “We need to leave right away.” 

Michael started to rifle through the clothes in the corner of his closet. The clothes that Cas kept there to hide the burlap that Dean had given him with his toys. 

“Father, no!” Cas panicked, throwing his covers off and shooting over to stop his father from rustling around in his things. Michael looked at him with a curious look and an open mouth. “I-I mean, it’s not over there. It’s in my dresser by the window.” 

“Okay…” Michael said quietly; suspiciously. “Either way, you need to get a week’s worth of clothes packed. We’re leaving as soon as you have your things together. Meet me down at the carriage when you’re done.” 

“Wait, father,” Cas called out quickly. “Where are we going? Why do we need to leave now?” 

“Her Royal Highness, Princess Meg of the Kingdom of Hell’s husband has passed away,” Michael said, beaming to himself. “It’s perfect. Now we can forget about the business proposal and we can focus on a marriage proposal instead. A marriage would be even better than a stupid fucking business proposal.” 

Cas felt his arms going numb.  _ This can’t be happening.  _

“Oh, Castiel! It looks like God is looking down on us in favor. He wants this to happen! He wants Dean Winchester to die. And He wants it to be at my hands, commanding the most powerful army in the world to hunt him down!” 

“No…” Cas whimpered, clutching his stomach as he felt bile rise in his throat. “Father, please, no. I don’t want to marry Meg. I don’t—” 

“You’ve ruined this for me once before, Castiel.” Michael stepped into Cas’s personal space, a dangerous, downright murderous look on his face.  _ “Do not _ do it again. Or I’ll do something worse than locking you in your room for a week.  _ Don’t test me.” _

Cas couldn’t tear his eyes away from his father’s. He didn’t realize that he’d been backing up until his back hit the wall and he let out a soft, “Oh.”

“You’re good for one thing, and one thing only. Do you understand?” 

“Y-yes, father,” Cas whispered meekly, doing his best to make himself seem smaller than he was. “I-I-I’m sorry.” 

“Get packed.” Michael turned on his heel and walked out of Cas’s room, leaving a sour taste in Cas’s mouth as he did. It took everything Cas had not to run into his bathroom right then and empty his stomach in the toilet. He couldn’t afford to waste that time throwing up instead of packing. If he did… He didn’t want to think what his father would do. 

Cas speedily shoved enough clothes into his bag to last him a week, throwing in another two outfits; just in case. Afterwards, he raced down to the carriage. Or rather, carriage _ s. _ His father was already in his own carriage with a random man Cas had never seen before. That took him by surprise and he stopped, looking into the bigger carriage in confusion.

One look from how father as the door to his carriage closed snapped him right back into motion and he handed his bags to a butler, thanking them before he stepped up into his carriage, that, only a second after the door closed, lurched into action. Cas could hear the driver yelling out to the horses to get going. A dread settled over Cas the farther they got from his house. The farther they got from the docks, if he were being honest. 

Being alone at the moment was not good for him. Cas wished that Dean was there, sitting next to him or even across on the other bench seat of the carriage so he could talk about what was going through his head. He could feel himself slipping into that headspace he put himself into where nothing phased him or remotely bothered him. This time felt different, though. This time, it felt a bit more severe. Possibly a bit more...permanent…?

“Stop it,” Cas hissed to himself, shaking his head to force the all around feeling of nothingness away. He closed his eyes, making himself think good thoughts about Dean, Gilda, Charlie, Sam, Benny, Lisa and Ben—anyone from the Impala. That was one cure he had found worked when this happened. Most of the time it worked, too. 

This time...not so much. 

~

It was around noon when the carriages stopped and Cas was ushered out. He was told to follow his father and before he knew it he was standing behind his father as he spoke to the King of the Kingdom of Hell: His Majesty, Crowley. Only every few words Michael spoke made sense. The others were just white noise to Cas. 

“Castiel...your daughter’s hand...marriage...I have plans...for after their union….in regards to...Dean Winchester...Of course, I’d need your blessing, but…”

Cas couldn’t bear to listen anymore. He hadn’t been fully listening in the first place, but after hearing Dean’s name, he knew what his father was most likely saying. There wasn’t any point in trying to listen anymore. 

Well, until Michael stopped and Crowley turned to his daughter and the two began whispering. Cas flicked his attention to see his father standing ramrod straight, a nervous expression carefully and meticulously hidden behind a mask of confidence and charm. That might be one thing Cas had to hand to his father: deceit. Michael had spent his entire life building up an arsenal of masks for any and every occasion. Cas didn’t think that there had ever been a time in his life that his father was left floundering for words when someone talked to him. 

“Novak,” Crowley’s voice sounded abnormally loud in Cas’s ears. “We will have to think about your son’s proposal.” 

Cas perked up at that announcement. King Crowley was not one to make decisions in a timely manner. He preferred to...well, abuse his power and push peoples limits. It took just over six months for the King to even accept Michael’s first appeal to meet years ago. Since then, Michael and Crowley’s relationship had mostly been Michael asking a simple question and then getting an answer months upon months later. It was ridiculous, if Cas said so himself. But right now, Cas couldn’t be more happy about that fact. 

“Your Majesty.” Michael took a small step forward and bowed his head. “I mean no disrespect by stating this, but your daughter will be nearing forty in a few years while my son is fifteen years her junior. There is no better time for them to wed and produce an heir for the throne,” he finished, giving the King and his daughter a bright smile. 

“I understand,” Crowley said. “Seeing as my daughter’s previous husband came to an…untimely demise in a hunting accident before producing an heir, I’ll keep that in mind while I think this proposal over.”

“Your Majesty—”

“You may be on your way back to Heaven, Novak. There isn’t much light in the day left, so I advise you get going now,” Crowley said, giving Michael a smile before standing. Cas bowed, discreetly looking towards his father to gauge his reaction. Michael forced himself to smile back, bowing deeply just as Crowley left the room with Meg following closely behind him. 

As soon as the royalty was gone, Michael snapped back up and glared at Cas, speaking with a clenched jaw, “Let’s go.” 

“Yes, father,” Cas said, doing his best to hide the giddiness he felt. Seeing as Crowley would take at least six months to get back to Michael about the proposal, Cas was safe. He’d be gone with Dean in three and never have to deal with his father’s nonsense again. Everything was working out in his favor.

~  ~  ~

_ November 13, 1695 _

 

“We’re having a party,” Charlie said. Cas hadn’t even taken two steps on deck before she’d run over to him and informed him of said party. “We got new mates!” She ran off, leaving Cas standing still and in a bit of a haze. 

Looking around, Cas could definitely confirm that there was a type of party going on. He started forward timidly, searching for Dean. Right now there were only Dean’s second hand mates on deck. All conversing and laughing together. 

“And it’s Gilda’s birthday in a few days!” Charlie exclaimed, startling Cas as she ran by again. 

“Oh,” Cas said softly to himself. “Alright.” He darted his eyes around once more, looking for someone in particular, before giving up and starting to head towards the cabins. Before he got there, someone stepped right in front of him, effectively blocking his path. 

“Well, hello,” the man said, his voice coming out smooth and dark, in a way. Cas stumbled a few steps back, the stranger following him and crowding into his personal space. “You’re a pretty little thing.”

“Hello,” Cas mumbled uncomfortably. 

“I haven't seen you around,” he continued. “What do you do?”

“No, uh, I—”

“You know, it doesn’t matter,” he interrupted. “We can go over details later. Or not. Either way…” He leaned in closer to Cas, smiling in an obvious attempt to be seductive. “You’re gorgeous.”

“Thank you, but—”

“I’m sorry if I’m being forward, but do you want to get out of here?” He raised his eyebrows as his arm slid around Cas’s waist. “And...you know?”

“I’m sure I don’t know,” Cas said, trying to wriggle away from this man. “Can you please get your—”

“Sweetie,” the man interrupted again. “Don’t play hard to get with me. I can tell by the way you look that you’re just as starved for touch as I am.” He pulled Cas flush against him and craned his head to look over Cas’s shoulder, mumbling, “Maybe even more so.”

“Please let go of me, I—”

“Honey,” the man interrupted again. Cas frowned as he tried to get out of his grasp. “You’re practically radiating the need for someone to take care of you. I can be that man. I know exactly what you want.”

“No, you don’t,” Cas said. “If you knew what I wanted you’d let go of me.”

He leaned in, stopping so his mouth was right next to Cas’s ear, and whispered, “C’mon darling. Don’t be like that. Why not save the time and just go find somewhere we can be alone right now. Your so pretty and you need to be taken care of. You deserve a real  _ man  _ to—”

“Lucifer.” That voice. Cas knew that voice and he smiled as the man breaching his personal bubble, Lucifer, stiffened at the sound of Dean behind him. “What are you doing?” 

Cas saw Lucifer roll his eyes before craning his head around to look at Dean. “Is it against the rules to try and get with a pretty little twink on your ship or something?” 

“Not at all,” Dean said, raising an eyebrow. 

“Then why are you cockblocking me, mate? We were just about go below deck and get busy,” Lucifer said, turning to Cas and smiling lasciviously. “Weren’t we sweetheart?” 

“No,” Cas said, pushing at Lucifer’s arm and feeling a wave relief that he was able to get the man off him. “For as long as I live: never ever. And not even after that.” 

“What?” Lucifer gaped at Cas and Dean chuckled. 

“Lucifer,” Dean said, smiling as Cas came over and molded himself to his side. “Meet Cas.” He pecked Cas on the lips, sliding his arm around Cas’s waist as he looked back at a pale faced Lucifer. “My one and only.” 

“Oh…” Lucifer breathed out. “Dean, I had no idea. He didn’t tell me his name or anything and—” 

“You never asked,” Cas interrupted, glaring at Lucifer. “You barely even let me talk.”

Lucifer opened his mouth to speak, but Dean interrupted him. 

“It’s okay,” Dean said. “Just don’t make a move on my lover again. If you do, that’s when we’ll have problems.” 

“Yes,” Lucifer said. “Of course.” 

Dean forced an overly sweet smile onto his face and said, “Alright. Now if you excuse me and Cas, we’ll be going to my cabin to, well,  _ you know.” _ The smile Dean had on his face now was real and it was smug and boastful. It made Cas smile, too. “And Luci,” Dean threw over his shoulder. “It’s  _ Captain. _ Not mate.” 

Cas smothered his giggles as they began walking away from a tight-lipped Lucifer. “I knew I didn’t like him,” Dean mumbled as soon as they were out of hearing range. 

“I don’t like him either,” Cas said. “He kept interrupting me. He wouldn’t let me get more than five words out. And he kept looking at me like he wanted to eat me.” 

“Maybe I’ll have to get him off my crew the next time we leave. I don’t want him sticking around so he can continue to undress you in his mind,” Dean said, tightening his arm around Cas’s waist. 

“Perhaps,” Cas said, tugging Dean forward to their cabin faster. “Either way, I really need you to walk faster.” 

“Do you?” Dean laughed, quirking an eyebrow. 

“Yes,” Cas hissed, keeping his voice low as he continued. “I saw you dock this morning so I put in a plug in preparation for this very moment.” 

Dean’s mouth dropped open and he stumbled as he looked down at Cas. “You did not!”

Cas playfully rolled his eyes, a smile tugging at the corners of his mouth. “I guess you’ll just have to get me to bed to find out for sure.”

“Hell yeah,” Dean rushed out, grabbing Cas’s hand and practically dragging him to their cabin.

~

A few hours later saw Cas laid atop Dean, drawing lazy patterns on the man’s chest as they basked in each other’s after-sex-glow when Cas thought back to a certain descriptor Lucifer had used to describe him when he had all but told Dean to fuck off. 

“What’s a twink?” He asked.

Dean choked on his spit and started coughing, suspiciously sounding more like laughing. “You want to know what a twink is?” He asked, his voice just a tad raspy. 

Cas nodded. “Yes.”

Dean smiled and laughed, “Well…y _ ou.  _ You’re a twink.” 

“I’m a twink?” Cas asked, furrowing his brows as he thought about what Dean could mean. “What do you mean by that? What about me is a twink?” 

“Baby,” Dean laughed again softly, “Everything about you is a twink. I mean, usually twinks are described as blonde, but that’s not the be all-end all.” 

“Oh! You mean my appearance?” he asked. “I’m a twink because of my appearance?” 

“Yeah,” Dean said. “Attractive, boyish, slender, little to no body hair.” 

“Oh.” Cas said quietly, tilting his head to the side in thought. 

“What?” Dean asked, moving his hand to grip Cas’s hip. 

“Is that…Is that  _ good?” _ Cas asked, looking up at Dean. “I mean, is that a good thing to be?” 

“It’s not a bad thing,” Dean said. “I like that you’re a twink. But I would like you regardless.” 

“Alright...You’re not a twink are you?” Cas asked. Dean smiled in amusement. “I mean, you’re not boyish and you have body hair. But you are attractive.” 

“No,” Dean said. “I’m not a twink.”

“What are you, then?” Cas asked. “Are you anything?”

“I’m a stud,” Dean said, putting on the face he’d once told Cas was his Blue Steel. 

Cas huffed out a laugh at the look, asking, “What does that mean?” 

“It means I’m someone who is really good at pleasing their partner,” Dean said, only joking a little. 

“Hm.” Cas furrowed his brows in concentration. “Do I get any special talents for being a twink?” 

Dean couldn’t help the swelling sensation he got in his chest for Cas. “You’re special talent is being the best partner a man could ever ask for.” 

Cas smiled but shook his head. “That’s because of my personality.” He sat up on Dean’s lap. “What kind of special  _ sexual _ talents do I get? You get to be really good at pleasing me, but what do I get?” 

“What do you want?” Dean asked. Cas pursed his lips and squinted as he thought. His face was contorted into a look that was entirely too adorable and wholly Cas. 

“I want to be really good at something,” Cas drawled. “Something specific.” 

“Being really adorable all the time?” Dean suggested. 

“I’m not adorable all the time,” Cas said. “You’ve seen me sneeze. I make a weird face when I sneeze. Gabe laughed himself out of a chair one time.”

Dean quirked an eyebrow at Cas, his amused smile widening. “I can say for sure that the face you make when you sneeze isn’t weird, it’s actually quite adorable.” 

“I can feel my face when I sneeze and  _ I _ can tell  _ you _ that it isn’t cute,” Cas said matter of factly. “It is quite weird looking.” 

“If you say so,” Dean chuckled, resting his hands on Cas’s thighs. 

“I do. I do say so,” Cas said quietly. 

“I still think you’re cute when you sneeze, though,” Dean mumbled, making Cas smile shyly. 

“Anyway, we still need to figure out what my special talent is,” Cas said. He laid back down, settling himself on Dean’s chest comfortably before continuing. “Am I really good at something?” 

“Do you want me to answer that with what you’re really good at in bed or out of it?” Dean asked. 

“Both,” Cas answered, nudging Dean to lift his head so he could wrap his arms around the man’s neck. 

“Well, in bed, you’re really good at riding me—”

“I don’t ride you often, though,” Cas interrupted. 

“Doesn’t mean you’re not good at it,” Dean countered. Cas smiled against his neck, hugging him closer. 

“I love you,” he said. 

“I love you, too, angel,” Dean replied. “And out of bed, you’re really good at keeping me sane when things get rough,” he said, almost like he was shy. 

“I do?” Cas asked, looking up at Dean with wide, shining eyes. 

“Yeah,” Dean said. “Now, what am I good at out of bed?” 

Cas smiled softly. “You’re really good at paying attention to me. There’s never a moment where I doubt that you love me or where I get anxiety that you’ll fall out of love with me.” 

“Really?” Dean whispered, smiling happily at Cas. 

“Yes.” 

“That’s amazing,” Dean said and kissed the top of Cas’s head. “You’re amazing.”

“You’re pretty amazing, too,” Cas said, smiling and blushing lightly. 

~  ~  ~

_ November 14, 1695 _

 

_ “Castiel!” Michael yelled, shaking his shoulder so hard it actually hurt.  _

_ “What?! What’s happening?” Cas exclaimed, shooting up in bed. “What is it?”  _

_ “The letter has arrived!” Michael said. He held up a slip of paper and an envelope before shoving them at Cas and urging him to read it.  _

_ “ _ ‘Dear Mayor Michael Novak, I accept your son’s proposal for my daughter’s hand in marriage and expect to see you as soon as possible. The wedding is to commence the moment you arrive in the kingdom…’ _ ” Cas read. Bile made itself known more and more with each word. “ _ ‘...so I request your arrival at the quickest pace possible…’ _ ” _

_ “Get dressed, get packed, we’re leaving now,” Michael said, hauling Cas up and out of bed. He shoved him towards his closet and then left. Cas only had a moment to himself before he was being grabbed again and led out to the carriages. His father’s hand felt like ice on his skin. It chilled him from the outside in and made everything around him look to be turning to ice, as well.  _

_ “Father, I beg of you, please don’t make me marry the princess—” _

_ “Shut your pathetic mouth, you ungrateful little shit. Since you were born you’ve done nothing but disrespect and shame the Novak name and  _ me _. Now is the time for you to make up for everything, and you ask me to give up everything I’ve worked for?” Michael’s eyes burned with fury and rage. “You’re nothing, Castiel. Absolutely nothing and you believe you have the right to ask anything of me? Of anyone, for that matter?” _

_ “I…” _

_ “You’re not worth  _ anything _ ,” Michael sneered. “You’re nothing. The only chance you will ever have to mean something is by marrying the princess. So close your disgraceful mouth and do the only thing you’ll  _ ever _ be good for.”  _

_ The carriage stopped. Michael dragged Cas out and towards a chapel. Meg was already stand at the altar, saying  _ ‘I do,’  _ as they entered and made their way to stand in front of the minister, next to Meg.  _

_ “Do you, Castiel Novak, take Her Royal Highness, Meg of the Kingdom Of Hell, to be your lawfully wedded wife, to serve and obey, to have and to hold, from this day forward, for better, for worse, for richer, for poorer, in sickness and in health, until death do you part?”  _

_ Cas tried to shake his head no because he didn’t want this, but his father tightened his grip. Cas felt helpless as his father answered for him.  _

_ “He does.”  _

_ “I now pronounce you husband and wife. You may now kiss—”  _

_ Cas stopped listening. He couldn’t breathe. Meg was leaning forward while smiling crudely at him. Her normally brown irises looked black as coal and Cas felt like he was catching fire. His heart hammered against his rib cage so painfully that his vision started to blur. The last thing he saw before he felt like he was being pulled into an embrace so tight his bones started to snap and splinter were the whites of Meg’s eyes turning the same black her irises were.  _

 

Cas shot up in bed, breathing hard. He felt a sharp, intense hopelessness work itself up from his chest in the form of a sob. Dean was still asleep, if his snoring was anything to go by, and Cas quickly clamped his hand over his mouth before the horrible wail of the leftover distress from his dream could get out. He curled into himself and squeezed his eyes shut, willing the images of Meg in a dress and the minister standing there, bible in his hands as he married him to Meg. It wasn’t real, and it would never be real. Cas knew that. It was just a nightmare and the only power it held was the influence he gave it over himself. 

“Cas?” Dean’s said, sleep laced in his voice. “Why are you up? 

Cas slowly pulled his hand away from his mouth, taking a deep breath to keep himself in check. “Just a bad dream.” 

Dean pushed himself up and scooted closer to Cas, wrapping his arms around him. “I’m sorry, baby,” he whispered. “Anything I can do?” 

Cas leaned into Dean’s arms and turned to press his lips against Dean’s for just a second. “Just keep holding me for now.” 

“I can do that,” Dean said, kissing Cas’s temple before laying them back down and holding Cas close. “And hey, I’ve got some good news.”

“Yeah?” 

“Ash and Kevin have finally figured out how to improve our canons and the time estimated to upgrade them is three months,” Dean said.“So...we’re gonna be docked for three months while that happens.” 

Cas lifted his head, eyes hopeful and the small beginnings of a smile forming on his face. “Really?” He asked. 

“Really.” Dean smiled. Cas moved up to kiss Dean softly before settling against his chest, doing his best to push the remaining thoughts of his dream out of his head. He and Dean snuggled together and before long, Cas heard Dean’s snoring again. The noise soothed Cas a little bit. But there was still a trace of hopelessness that was there in his chest, sitting like a rock and making his heart feel heavy. 

~  ~  ~

_ November 25, 1695 _

 

Thanksgiving was tomorrow, but Cas was having just a tad bit of trouble feeling very thankful. There was this bone chilling feeling of dread that hadn’t left him since the night he had had that nightmare. The only good thing that had happened in the past few days was that Michael got called to a sister city of Heaven that was across seas by at least two days. It meant that Cas got to spend the next few days with Dean. 

“You look sad.”

Cas looked up from his plate to see Lucifer. He rolled his eyes and glanced around the mess, noting where everyone was. Dean was with Benny, Lisa, and Sam in the drawing room going over a few last details before the feast, so they were nowhere to be seen. Charlie and Gilda were sitting together, Charlie in Gilda’s lap, while Jo was next to them both, smiling and laughing. If Cas didn’t know better, he would definitely say that the three of them were...flirting? It was quite a sight. 

“Why?” Lucifer tried again. Cas looked at him and scowled. 

“I’m not sad,” he grumbled. Lucifer leaned back in his chair and raised an eyebrow. 

“And I’m not blonde,” he snorted. “C’mon, tell me what’s wrong. You can trust me.” 

Cas glared at the man. “Why in the world would I trust you? Not only do I not know you, but I don’t like you, either.” 

“Ooh,” Lucifer winced playfully and sucked in air between his teeth. “That hurt.” 

“Sure it did.” Cas rolled his eyes again, looking away from Lucifer’s smirking face. 

“Well, look, you may not like me, but I like you,” he said in a way that sounded as if he was confessing some deeply kept secret. “So, I think we have a good chance of being able to fix our relationship.” 

“What relationship?” Cas pushed away his plate of salad. The one he’d made up a hour ago when he came in here, after Dean had been called into the drawing room, and had only eaten a few bites of. “We do not have a relationship.” 

“Now you’re just trying to hurt me,” Lucifer pouted. “Can I ask you something?” 

“I will not answer,” Cas said. 

Lucifer stared at him intently, huffing after a second and shaking his head. “Okay, forget my question from before, let’s go this route: why don’t you like me?” 

Cas stared blankly at Lucifer, giving him nothing. “Will you please leave me alone? I feel I’ve made myself very clear about what I want regarding you.” 

Lucifer’s face fell and he leaned forward in his seat. “Why are you with Dean?” He asked in a hushed tone, eyes wide and curious. There was a little bit of pain in there that took Cas off guard. His walls crumbled a bit and he found himself growing curious to where Lucifer was headed with this conversation. 

“I don’t understand the question,” Cas said cautiously. “I love him.” 

“And you think he loves you?” Lucifer scoffed. Cas recoiled by pushing himself up and out of his chair. 

“Leave me alone,” he said firmly. “Don’t speak to me again.” 

Cas stepped away, aiming to get out of the mess and find something else to do. Maybe Ben and Ash would like some company. Hannah said she didn’t have anything planned tonight, and Cas found that she was one of the only new recruits he got along with really well. He very much liked her company. 

Lucifer’s voice followed him, though, and Cas picked up his pace. 

“Cas, wait!” Lucifer’s hand clamped around his wrist and yanked him back and he glared angrily into sickly blue eyes. “Cas, look, I’m just worried about you. I don’t want you to get taken advantage of.” 

“You don’t know me, you don’t know Dean, and you have no right to insert yourself into our relationship,” Cas growled, jerking his arm out of Lucifer’s grip. 

“Give me a chance?” Lucifer whispered pleadingly. Cas froze in place.

“What?” He hissed, absolutely bewildered by Lucifer’s words and actions. 

“I bet I can make you happier than Dean ever could. I can make you feel so good, Cas, I can—”

“ _ Are you fucking  _ insane?!” Cas almost yelled. “You’d have to be  _ completely _ out of your fucking mind to say that.” 

“I—”

“Did you not hear a word I just said? I love Dean, he loves me. You have no right to insert yourself into our lives and start telling me what you can do for me. You don’t know Dean, you don’t know me—you don’t even know my full name! So do yourself a favor and leave me the fuck alone,” Cas was seething. He felt his Grace bubbling to the surface and used it to his advantage. The air around him shimmered with energy and his vision started changing, slipping into another dimension and showing him glimpses of the souls of the people in the room instead of their physical bodies. Lucifer’s was dark. A blood red and it unsettled him. “If you don’t leave me alone, Lucifer, I promise you I will disable you. Do you understand? Nod if you understand me.” 

Lucifer nodded, eyes wide and face a little pale. Cas pivoted around and walked out of there with confident steps and his head held high. 

 

_ November 26, 1695 _

 

“There’s so many people,” Lisa said, a wonder-like quality to her words. “There’s never been this many people here on Thanksgiving.” 

Cas looked out at the mess packed with people. Every table was filled to capacity and there were people who had to stand while holding their plates and eating. Benny had been working all night and all day to prepare this massive feast. Turkey, chicken, pork, and beef all prepared in several different ways. Potatoes—mashed, baked, scalloped, fried, and boiled. Rolls with butter, cranberry salad, twelve different soups, corn—on the cob and creamed, stuffing, several different kinds of gravy, and so many more dishes, too. 

“I’ve never had a thanksgiving like this,” Hannah said. “This is  _ massive _ .”

“Oh, yeah,” Cas shrugged. “I’ve never been able to attend one of their Thanksgivings, but they don’t joke around about it.” 

“He’s right,” Lisa murmured, scouting the crowds to see where Dean was with Ben. “They take this holiday the most serious out of all of them.”

“I think part of the size of everything this year is because Benny wanted to show off to the new crew members,” Cas said, poking at his food. He’d taken several bites of his food, but that was all. The food was good, but he didn’t have an appetite. “That or it was Dean who told him to make so much so that Dean could show off how great Benny is at that he does.”

“That’s probably it,” Lisa said, “Benny’s really humble. Dean’s the one who likes to show off and compliment.” 

Cas snorted and nodded his head. Dean did do that. He was humble when it came to himself, but if it was about the people he loved, there was no limit to how far he would go. 

“Cas, you’re not eating much,” Hanna said. Cas looked up from his plate and gave her a smile. 

“I’m still full from breakfast,” he said. She frowned at him and looked like she wanted to say more, but kept herself from saying it. 

“Did you try the corn pudding?” Lisa asked, bringing a forkful of said food up to her mouth. “It’s to die for.”

“I did,” Hannah said, “and I agree. It’s delicious.” 

Cas turned out as Lisa and Hannah continued to talk, surveying the room. His eyes landed on Lucifer in the farthest corner from him. He clenched his jaw in annoyance as Lucifer immediately pushed off the wall and headed towards the exit. That action told Cas that Lucifer had been watching him. 

Before he could get any angrier, movement from his right made him turn his head to see that Gilda had sat down next to him. 

“Hey,” She said. Cas let out a breath he hadn’t known he was holding and smiled genuinely at her. 

“Hello,” He said quietly. 

“You’re upset,” she said, no trace of a question in her voice, so Cas just nodded. “C’mon.” Gilda gave him a smile, standing back up and pulling him with her. “Let’s go for a walk, yeah?” 

“Yeah,” Cas said, waving a goodbye to Lisa and Hannah before allowing Gilda to tug him along. She took him out of the mess and up to the quarterdeck, letting him get comfortable looking out at the ocean before speaking up again. “What’s got you like this?” 

Cas rested his chin on his hands and breathed deep before answering. “I had a bad dream about a week ago.” 

“Ah.” Gilda said. 

“Yeah, and ever since I’ve been feeling like something bad is going to happen. Like there’s another shoe that’s about to drop,” Cas explained. “I’m so close to happiness, you know. But there’s just this little voice in my head that telling me that something will happen to keep me from it.” 

“Have you talked to Dean about this?” Gilda asked. Cas shook his head, closing his eyes as a slight breeze rustled his hair. 

“No,” he said, “I haven’t.” 

“Why not?” 

“If I talk to him about this and then in a few months everything goes according to plan, I’m going to feel so stupid,” Cas said. He saw Gilda nod her head from his periphery. 

“Will you tell me about it?” She asked. 

“Yeah,” Cas said, nodding. “Uh, well, it started with my father telling me to pack because we got a letter from the kingdom saying that our presence was requested. So, we go and when I get there, Meg is in the chapel with a minister and she’s saying ‘I do’. My father drags me up to stand opposite her and the minister asks me if I take her hand in marriage. I want to say no, of course, but I’m frozen in fear and my father answers for me and the next thing I know… The minister’s said ‘you may now kiss the bride’ and Meg is leaning in to kiss me. Her eyes had gone black and I felt trapped. Like someone or something was holding me and squeezing the life out of me,” Cas finished, taking another deep breath. “It was terrifying.” Gilda moved over and put her arm around his shoulders, giving him a reassuring squeeze. “But, it was only a dream,” Cas said. He felt Gilda nod in agreement. 

“I saw you talking to Lucifer the other day,” Gilda said after a while. “You didn’t look very happy. What was that about?”

Cas rolled his eyes and shook his head in irritation as he remembered what Lucifer has said. “I hate that man. He’s been harassing me for a few days. Nothing serious. What you saw last night was me handling it.”

“Oh.” 

Cas could sense her unasked question. “If he gets any worse, I’ll tell Dean, but as it stands right now, I don’t need Dean to come and save me. I’m fully capable of taking care of myself.”

“I agree, I agree,” Gilda said, holding the hand she didn’t have rested on Cas’s shoulder up in an ‘I surrender’ sort of gesture. “But, Cas, if I was in Dean’s position, I’d want to know if someone was coming onto Charlie.” 

Cas considered her words, eventually sighing and nodding his head. “You’re right. I’ll tell him.”

“I think that’s the right decision,” Gilda said. Cas smiled out at the water in agreement, keeping silent before he remembered what he’d seen in the mess the same night. 

“Hey!” He said, startling Gilda just a bit. “What’s going on between you and Charlie with Jo? I saw you guys in the mess, too, you know. And if I didn’t know better, I’d say you looked like you were flirting.” 

Gilda laughed and nodded her head. “We were flirting with Jo.” 

Cas turned to look at her with wide eyes. “You and Charlie were  _ flirting  _ with Jo?” 

“Yeah,” Gilda laughed. “I love Charlie and she loves me, but that doesn’t mean we can’t have a little fun with someone else from time to time.”

“You…” Cas floundered for words. “How long have you been flirting with Jo?”

“Honey,” Gilda said, “we’ve been doing more than just flirting.” 

“Oh, Gods.” Cas gaped at Gilda. 

“Yeah, and let me tell you, Jo’s amazing with her tongue. I mean she just—”

“No, no, no!” Cas slapped his hands over his ears. “Hush! I don’t want to hear about your sex life!” 

Gilda threw her head back as she laughed. “Okay, okay,” She said, pushing Cas’s hands away. “Okay, I won’t say any more about how  _ fantastic _ Jo is in bed.” 

“Gilda!” Cas groaned, smiling along with Gilda as she laughed again. 

They stayed silent for a long while, looking out at the ocean and breathing in the fresh air. It wasn’t until Cas had yawned his third yawn that Gilda lifted her head and patted his shoulder. 

“Perhaps you should get some rest, huh?” 

“Yeah, probably,” Cas said quietly. He let Gilda guide him to his and Dean’s room, waiting until she left and after she said goodnight to undress and get into his night clothes. After that, he snuggled under the covers of his bed and closed his eyes. 

He was able to get to that place where he was almost asleep, but not quite, when he was woken again. 

“Hey, sweetheart,” Dean said softly, running a hand through Cas’s hair and smiling at him as he opened his eyes. “Gilda said you were tired. And you may need some extra loving tonight.” 

Cas yawned and shook his head. “‘M fine. You go back to the mess. Come to bed when you’re tired.” 

Dean leaned forward and face Cas a kiss on the head, standing back up and leaving Cas in bed. Cas closed his eyes for what felt like only a second before the bed dipped and a warm body slid up against his. He opened his eyes and smiled as he saw Dean settling in. 

“I thought you left,” Cas hummed, unable to resist snuggling in closer to Dean’s warmth. 

“Eh, I’m tired now,” Dean said. Cas could tell he wasn’t actually tired. His voice was awake and alert, but he wasn’t going to try and convince Dean to leave. Instead, he was going to be a bit selfish and keep Dean for himself. 

“Hey Cas,” Dean whispered, resting his chin on top of Cas’s head. 

“Yeah?” Cas said, yawning. 

“You know, I don’t want to imagine a future without you in it. I  _ can’t _ imagine a future without you. I won’t; because you’re it Cas. You’re my future,” Dean whispered. Cas dug his face into Dean’s chest and sighed, willing himself not to cry. He didn’t have a reason and he’d feel silly for getting so worked up in the morning.

“You’re my future, too,” he said, his voice muffled. 

“You know, I would swear to you that I couldn’t love you more than I do right now, but I would be lying because I know I’ll love you more tomorrow. Every day I fall deeper in love with you than the day before,” Dean said, hugging Cas even tighter. “I love you so much, Cas. I will until I die. And if there’s a life after that, I’ll love you then, too.”

Cas hugged Dean tighter in return. Both to get closer to Dean and to hide his face because he knew he was just about to cry. He was tired and it made everything Dean was saying was so overwhelming. “But, squarely, love isn’t a strong enough word to describe how I feel about you.” 

Cas nodded his head, completely understanding what Dean meant. He felt the same way. 

“You make me feel I am alive. Other men have said they’ve seen Gods come down from the Heavens and speak to them with voices of liquid gold… But I don’t need to see or hear any God. I don’t need them, Cas. Not when I have you.” 

Cas squeezed his eyes shut and smiled into Dean’s chest. That feeling of dread was easing out of his chest. 

By the time he fell asleep, he was content. He and Dean had shifted and Dean’s face was pressed into the crook of his neck, but they were still wrapped around each other, and Dean was still whispering sweet words to him.

**Notes for the Chapter:**

> Okay, so, the announcement I talked about in the beginning notes:  
> I'm thinking of rewriting this fic. Probably shortening it and taking out some major plot points of this fic. It'll still be the same idea (Dean's a pirate, Cas is the son of his worst enemy, they meet, they fall in love, stuff goes down and Cas almost is married to a woman, but Dean comes in at the 11th hour and they live happily ever after). 
> 
> The reason is because I'm not entirely happy with how I've written this fic. I don't like my actual writing, and I don't like the plot points that I've added and how I've strayed from the tumblr post that inspired this fic. And I believe that there's way to much smut. (It's in almost every chapter. It's gone past too much smut.) I can partially attribute that to the fact that I did start this fic right when I got into writing smut, so I got totally carried away. I sincerely want to apologize to you all for that. It's probably been very tiring to read. 
> 
> Plus, my writing isn't... Great. It's very underdeveloped. I've come so far since I began this fic, and whenever I sit down to continue writing, I fall back into the headspace I had when I first started this fic. It's a dangerous place to be because you get more dialogue than description when more description would be better. Not only that, but this fic is also all over the place. I've put in useless scenes that don't advance the plot and it's just... Wow. Not great. (And all the historical inaccuracies???? Oh man, I want to slap myself.)
> 
> ALSO I discovered how much I actually really like the ABO Dynamics universes a few months ago and I feel like I missed this huge opportunity. (At first, I was going to write this one as ABO but a friend of mine that was supposed to be a sort of beta for me didn't like ABO and I didn't want to make her uncomfortable reading it, so I took her advice and introduced Meg as Crowley's daughter for Cas to marry.) I'm not sure if the new fic will be ABO or not. I haven't decided. What would you all think? ABO or not ABO? (If you're even going to read the new version, I mean.)
> 
> Lastly, the new version won't be posted for a few months, most likely. I've got other projects I've got to work on (original projects) and I've got school I need to think about, so... It'll be a while. 
> 
> Thank you everyone who read this far! You have all of my thanks! 
> 
> Let me know what you think about the chapter, my thoughts about the new version of this fic I'll be writing, or just tell me your favorite part of nature. Whichever tickles your fancy. :P 
> 
> Once again, thank you so much! I love you all with my entire freaking heart.


	17. Chapter 17

**Notes for the Chapter:**

> It's my birthday so here's an extra special birthday chapter!!

_ January 18, 1696 _

 

Cas couldn’t concentrate. His focus had been slowly slipping out the window every day it got closer to Dean’s birthday. Now he was just counting down the minutes because there was only  _ six days _ left until he got to leave his father. Of course, they wouldn’t be able to leave then yet. The canons still needed a few more weeks before they were fully done being updated, but in six days Cas got to pack up and stay on Dean’s ship until they were done and they could depart to the ocean.  _ Six days!  _

Not even the anger of his father and the consequences that came with it could dull his excitement. 

His father was yelling at him now, shouting about how disappointed he was. Usually, Cas would be apologizing and asking for forgiveness, but not today. Cas couldn’t feel sorry for not living up to his father’s impossible standards when he would be gone within the week. Not only that, but it was an hour past sunset and Dean was expecting him. He was so anxious to get out of the house that the slap his father delivered him took him by complete surprise. It sent him stumbling into the wall of his father’s study. 

“I should’ve let you die all those years ago in that room! You’re no use to me!” Michael yelled, storming over to Cas. He grabbed Cas’s collar and cocked his other arm back, getting ready to hit Cas, but a knock at his door stopped him in his tracks. 

Michael scowled at Cas, but let him go. “Pathetic,” he spat before walking over to answer his door as Cas stood as still as he could against the wall. Keeping his movement to a minimum meant less of a chance of angering his father again. 

“What?!” Michael snapped at the person on the other side of his door. 

Cas heard someone with a small voice say, “I’m sorry, Master Novak, but a letter from the Kingdom came for you.” 

Michael’s angry expression fell and morphed into a surprised and hopeful one. “A letter from the kingdom?” He barely got his voice above a whisper. 

“Yes, Sir.” 

Michael snatched the letter from the servant outside of his door and slammed it closed, almost floating over to his desk and sitting down. He ripped it open and read furiously. 

“Castiel…” he breathed out. He looked up and a wide, sick smile spread across his face. “You’ve finally proven to be useful.” 

“What?” Cas whispered, hesitantly pushing off the wall and walking over to his father’s desk. 

“We leave first thing in the morning.” Michael said, getting up and handing the letter to Cas. Cas read it carefully. 

 

_ ‘Dear Michael Novak, _

_ His Majesty accept your son’s proposal of marriage to Your Majesty’s daughter, Her Royal Highness, the Princess Meg of the Kingdom of Hell.  _

_ Return to the Kingdom of Hell as soon as possible. Your Majesty has said there is much to do before the wedding is to commence. _

_ Your Majesty, _

 

_ King Crowley.’ _

 

Cas saw his father moving past him, grabbing things from his shelves and desk while speaking, but none of it was heard by Cas. He was too busy reading and rereading the letter. His nightmare was coming true. He was right to be upset by it. Everything was falling apart.

Cas sprinted from his father’s study, running to his own room and slamming the door shut. Tears streamed down his face as he collapsed onto his bed. This couldn’t be happening. This  _ shouldn’t  _ be happening! Everything was going so well. The canons were almost finished being updated and he was so close to leaving when they were! 

Crowley wasn’t supposed to reply to them in a timely manner. He was supposed to take months like he usually did. This wasn’t fair! Cas was so close to happiness and freedom and family. 

“Cas?” Cas heard Dean’s voice from his window. A second later he saw his head pop into view. “You didn’t come at sunset and I got worried. What’s kept you—Cas?!”

“Dean!” Cas cried, reaching out for the man. “Something terrible has happened! Something awful!” 

“What’s wrong?” Dean asked as he strode over to Cas’s bed and sat down, taking Cas into his arms. “What happened?” 

Cas lifted the letter up for Dean to see. “Crowley wrote back,” he said, “saying he’s accepted my father’s proposal.” 

“Oh,” Dean said. Cas buried his face in Dean’s neck and cried, gripping onto him for all he was worth. Dean leaned forward to put the letter on Cas’s bedside table before he scooted back and laid down with Cas, hugging him tight. “Just go to sleep, Cas. When you wake up, everything will be okay.” 

“Dean,” Cas cried, shaking his head. “How?” he asked, shoulders shaking. “I leave in the morning and the canons aren’t done. How will this be okay?” 

“I won’t let you go, okay? I’m never letting you go,” Dean whispered. “Just go to sleep. Everything will be okay.” 

Dean held Cas until his shoulder stopped shaking. He didn’t let go until he felt Cas’s breathing even and his body slump. After that, Dean untangled himself and kissed his temple before getting up and searching for a bag for Cas’s stuff. He didn’t know what all Cas would like to take, but packing Cas’s clothes seemed like a good place to start. 

Dean moved to Cas’s closet, sliding the door into the wall and looking in. He saw a small knapsack and smiled as he realized what it was. The fabric was worn and looked well used. He could almost see through the canvas into the bag and something caught his eye. Something rather big and long. Dean reached down and picked the knapsack up. He looked into it and his eyes widened. Cas hadn’t been kidding when he said he’d gone and bought himself his own toy. 

This thing was a monster of a pseudo-penis. Bigger than he was, for sure. When Dean wrapped his hand around the shaft of it, his finger’s didn’t touch. It was longer, too. A tad bit of jealousy flared up in him, but he squashed it down. This was a  _ toy _ . He would not get jealous of a toy. 

Dean put the object back in the knapsack and put it out of his mind. He had a task to complete and obsessing over whether he was big enough for Cas was not something he had time for. 

Almost a half hour later, Dean had finally found Cas’s bag and was stuffing it with clothes. He was in the middle of folding a shirt when he heard something from outside of Cas’s window. It sounded like the leaves from the vines growing on his trellis. Tonight there was no breeze, however. 

Dean slowly turned and made his way to Cas’s balcony, squeezing his hands into fists in preparation of a fight, if need be. He cocked his arm back and got ready to strike as a head popped up over the railing. Dean stopped in his tracks, though, as he saw who it was.

“Sam?” He asked, letting out a breath of relief before going over and helping his brother over the railing. “What are you doing here?” 

“We got a message from Abbadon,” Sam said, “she’s taken Lawrence captive.” 

Dean felt like he’d been punched in the gut. Lawrence was where Jess and Andrea lived. 

“She has Jess…” Sam said, his voice breaking. “A-and she’s got Andrea. She’s got them. She’s got Benny’s and my—”

“We’ll go get them,” Dean said, stopping Sam from spiraling out of control. He turned to go wake Cas up so they could get him all packed and ready to leave, but Sam grabbed his arm and stopped him. 

“She’s got help, Dean,” Sam said. “Her letter said a few pirate crews joined her.” 

Dean nodded. “Which crews?” 

“The Hellhound Pirates, the Garrison Pillagers, the Demons of the Sixty-Six Seals, the Ghost Devils, the Leviathans of Purgatory, a few more significant crews.” 

“That’s a lot of pirates,” Dean said, more to himself than to anyone else.

“It’s a company, Dean,” Sam said. “She’s got almost a full platoon more of people than we do.”

Dean looked at his feet, nodding his head and closing his eyes. “She doesn’t have our people, though. Abbadon has pirates, yes, but she doesn’t have my pirates. We can win against her. I know we can.” 

“But, Dean, she—”

“She doesn’t stand a chance,” Dean interrupted. “We set sail immediately.” 

Sam was silent. A heaviness settling in the air between them as Dean lifted his head to look at Cas on his bed. Sam asked, “What are you going to do about Cas?” 

“I…” Dean battled himself in his head. On one hand, he wanted to take Cas with. On the other hand, there was a good chance that a lot of good men and women would be lost fighting Abbadon. 

Dean wasn’t willing to let Castiel be one of those men. 

“You’re not going to take him with,” Sam stated, no trace of a question in his words. Dean nodded his head in answer, still. 

“I won’t risk him,” Dean said.

“He’s going to be upset with that,” Sam said. “He probably won’t let you leave him.” 

“He has no training for fighting,” Dean said, squeezing his eyes shut for a quick second before moving over to Cas’s bedside table. He searched through it for a pen. “If he comes with us, it’ll be a death sentence for him.”

“That’s… Yes, that’s true, but—” 

“But nothing.” Dean finally found a pen. He grabbed Crowley’s letter and flipped it over, debating on what to write. “I’m confident that we’ll be able to neutralize Abbadon in no more than four months. Her getting all these pirates together likely has a sloppy chain of command. Sloppy chain of command means sloppy orders. Sloppy orders means sloppy soldiers. Sloppy soldiers mean easy targets.” 

Sam sighed. “Dean.” 

Dean gritted his teeth and quickly wrote a short note to Cas. He was certain that Cas knew that he wouldn’t just leave him. Not unless he had a good reason. However, he knew that Cas would be upset with him for not taking him with. As the saying goes, better to ask for forgiveness than for permission. 

“I won’t risk him,” Dean whispered, setting the pen down next to the letter and then heading back over to Sam. “Let’s go.” 

Sam looked about ready to argue, but Dean pushed him out to the balcony. Sam didn’t argue after that, and swung himself over the railing, descending quickly towards the ground. Dean, on the other hand, swung a leg over and stopped, looking at Cas with a sad expression. He was tempted to say  _ fuck the odds _ and take Cas with him, but he couldn't. 

Crowley was one for dramatics. He would spend a year or more planning Cas and Meg’s wedding and it would not take years to defeat Abbadon. 

Cas’s door opening made Dean’s heart leap and he immediately tried to swing himself completely over the railing. He cursed as the fabric from him pants got caught, waiting for Michael to storm over to him and probably push him over the edge to his death. 

When that didn’t happen, Dean looked up and into the eyes of a kid about Cas’s age. He looked at the kid’s outfit and came to the conclusion he was a servant. 

“You…” the kid said, his eyes wide when Dean looked back into them. “You’re, you’re D-Dean—“

“Yeah,” Dean brushed him off, “I’m the Pirate King. Now, look, kid, do me a favor?” The kid nodded and Dean looked over to Cas one last time. “Don’t wake him up until my ship has set sail. And when he is awake, look after him for me? He’s the love of my life.”

“O-okay,” the kid said. 

Dean looked back at Cas, smiling softly as he freed the fabric of his pants. “Tell him I love him, too, please?” 

The kid nodded again. Dean gave him a smile before swinging over the railing and descending to the ground next to Sam. 

 

~ ~ ~

 

_ January 18, 1696 _

 

When Cas woke up, he greeted to early morning rays in his face. It took trying a few different positions before he found one that didn’t blind him, but by then he was fully conscious and the events of the night before caught up with him. 

Cas shot up in bed. The first thing his gaze landed on was his bags, packed and slumped against each other at the end of his bed. He could feel panic starting to quicken his breathing, so he launched himself off his bed and onto his balcony. 

Dean’s ship was gone. Dean’s ship was gone and he wasn’t on it. Cas turned around, gripping the edge of the balcony’s railing and trying to make sense of what was happening, but all he could focus on was the fact that he wasn’t on the Impala, and Dean was gone. 

His heart was beating against his rib cage. His stomach felt like it’d fallen into his feet, and his vision blurred. Thoughts like, ‘ _ What was happening?’, ‘Where is Dean?’  _ and  _ ‘Why am I not with him?’  _ ran through Cas’s head. 

He pushed himself off his balcony and made his way over to his bed, collapsing onto the edge, creating a gust of wind that fanned out around him. The flutter of paper drew Cas’s attention to his night stand. On it, he saw the engagement notice sitting there, face down and held down by the pen sitting on an edge of the paper. 

Cas reached over and grabbed it, holding his hand over his mouth as he read the two words written in Dean’s distinct scratchy handwriting. 

_ “I’m sorry.” _

Cas dropped the paper, looking up at nothing in particular as his heart shattered into dust. Dean…

Dean left him? 

Dean... Left… Dean left him. 

A silent scream worked its way up Castiel’s throat, tearing at his vocal cords and burning his throat raw. Cas slid to the floor, his back against his bed, and sat still. He had absolutely no idea what to do. He was in shock, staring at nothing while a million different thoughts ran through his head at lightning speed. One thought after another, one though interrupting the other before it got to finish. Nothing made sense. 

A knock at his door made Cas’s Brain short circuit. 

“Master Castiel?” He heard from the other side of his door. “I’ve been sent to fetch you and your bags.” 

Cas opened his mouth to try and answer, but nothing came out. 

“Master Castiel, I, uh, I also have a message for you,” the person continued. “From, uh, from Dean.” 

Cas was up and opening his door in an instant, pulling a servant he’d never seen before into his room. “What did Dean say? Will he be back? Did he say when?” 

The servant, a tall dark blonde boy, around Cas’s age or younger, stared at Cas with wide eyes. “I’m not sure,” he said, “All Dean said was to tell you that he loves you.” 

Cas shook his head. That couldn’t be it. “What else? What else did he say?” 

“Uh, w-well he told me to, uh, to look after you. He said you were the love of his life,” the servant boy said. Cas gripped his shirt tightly, shaking his head again. He would not accept that. 

“There was nothing else he said? No word of when he’d be back?” Cas asked. 

“No, no word for when he’d be back. He only asked me not to wake you until his ship was gone, and then told me to look after you,” the servant said. Cas felt his knees shake and he shook his head as he backed up to his bed again. 

“That can’t be it,” he said, shaking his head vigorously. “There has to be more. He had to have told you more!” 

“I… I’m sorry,” the boy said. “That’s all he told me.” 

“But… But he promised he’d take me with him,” Cas said, his voice cracking as feelings of abandonment and hopelessness and betrayal flooded through him. “He promised… He...”

“I’m sorry, Master Castiel,” the boy said quietly. “My name is Samandriel, but most call me Alfie. I’m to be your manservant.” Cas looked up at him blankly, not comprehending what he was saying. “Master Castiel, we have to get going. Your father sent me up here to collect you and your things so we could get going to the Kingdom. He told me not to keep him waiting. He wants to leave now.” 

“I… What?” Cas shook his head slowly. “I don’t know what you said.” 

“I’m sorry, Master Castiel, but we need to go. Your father wants to leave now,” Alfie said. Cas only blinked before standing up and grabbing his bags. He worked on autopilot as he descended the stairs and walked out to his carriage. He was in shock and didn’t know what to feel regarding Dean. There was so much hurt and betrayal surrounding his name, but Cas couldn’t feel any of it. Not at the moment, anyway. He was certain that he’d break down sometime, soon, thought for now, he was okay to deal with the void inside him. It would be better to break down some place that he was safe. 

Alfie followed behind him, though, and Cas could practically taste the confusion radiating of him. His presence gave Cas the thought that he should be guilty because Alfie had been forced into the drama between him and Dean. He’d been made to make a promise he didn’t know the weight of. 

Some time into their carriage ride, Cas mustered up the energy to say, “I’m sorry.”

“For what?” Alfie asked, looking at Cas curiously. 

“For Dean,” Cas said. “For the position he put you in. I don’t expect you to take care of me. Not the way he wants you to.” 

“Master—”

“You can call me Cas. I’d prefer it,” Cas interrupted. 

“Well, Cas, I, uh, it’s my job to take care of you. It’s what I was employed for, actually,” Alfie said. Cas shook his head. 

“That’s not what I meant,” Cas said, “I know Dean, and he expects more from you than an employee should give. You don’t know the load Dean has put onto your shoulders.” 

“Cas,” Alfie started slowly, seemingly concentrating hard on his choice of words, “I’m not sure exactly how to say this, but to put it bluntly, I’d like to be able to take care of you as a friend would take care of another friend.”

Cas stared at Alfie blankly. “What?” he said. “Why?” 

“I may be new to employment for your father, but I’m not new to Heaven. I’ve been here for quite a few years and believe me, you’ve got a reputation,” Alfie said.

“I am the mayor’s son. Of course I have a reputation.” 

“No, I mean apart from your father,” Alfie said, “you’re held in high respect. You’re a good person, and people know it because you’ve been good to them. Your household servants don’t work for your father  _ for  _ your father. They don’t like him in the least, but they tolerate him for you because they care about you.” 

“I don’t know what you’re trying to say,” Cas said, looking away from Alfie. 

“I’d like to be your friend,” Alfie said. Cas looked back at him with furrowed brows and blank eyes. Alfie smiled at him and asked, “How did you and Dean meet?”

“We…” Cas studied Alfie for a second. He tapped into his Grace and examined Alfie’s soul, but he found no darkness in it. Alfie was being sincere. “We met the first night he ever docked at Heaven.” 

“How?”

“He thought I was a streetwalker,” Cas said. 

“He…” Alfie blinked in shock. “He thought you were a prostitute?” 

“Yeah,” Cas said. “He found out later I wasn’t, of course, but we still... Still spent the night together.” 

“Ah,” Alfie nodded his head in understanding, a small smile on his face. Cas quirked an eyebrow at him and shook his head. 

“You’re taking this surprisingly well for someone who’s just found out that the son of the mayor of Heaven is not only in a long term relationship with the most feared pirate in all of the seas, but also...” Cas said searched for a word.

“Queer,” Alfie supplied. Cas nodded his head slowly. 

“Yes,” He said, “You’re taking it like I’ve told you I like blueberries and honey in my oatmeal.” 

Alfie waved Cas off. “You should meet my brother. He has a lot of partners. Both men and women. And a few in between.” 

Cas’s eyebrows shot up in surprise. “In between?” He asked. Alfie nodded. 

“Some of his lovers are both man and woman, some are neither, some are a man in a female’s body or a woman in a male’s body, some are men who prefer women’s clothing or women who prefer men’s clothing, et cetera,” Alfie explained. “He lives on an ‘island of outcasts,’ as he says. They’re not really outcasts, though. Just misunderstood by the rest of the world.” 

“Ah,” Cas said quietly, going over the new information in his head.  _ Men who liked to dress in women’s clothes? _ “That’s really amazing.” 

“Yeah.” Alfie smiled. “So, how long have you two been together?” 

“This September it’ll be five years,” Cas said, feeling a jab of pain stab his heart. His walls were crumbling and he couldn’t do this right now. “We need to talk about something else. Anything other than Dean. Tell me about yourself.” 

“Oh,” Alfie gasped, floundering for just a second before launching into his life story. Cas listened intently to everything he said, almost memorizing everything as to keep his mind off of Dean. 

Alfie’s voice helped to ground Cas and strengthen his flimsy walls the whole carriage ride to the Kingdom. Cas was certain that by the time they got to the Kingdom, his walls would hold up at least until nightfall when he was alone in his room. 

He was right. Almost as soon as one of the servants started guiding him to his room, he could feel them cracking. 

Alfie was assigned to the room behind one of the large tapestries in Cas’s room, and Cas took comfort in that. He didn’t want to be alone, and this way he wasn’t. Not completely. 

As the sun descended and Cas finally felt the last brick turn to dust, he cried. He sobbed his lungs out, burying his face in a pillow to muffle himself. Apparently he didn’t do a very good job because the next thing he knew the bed behind him dipped and arms wrapped around him. 

“I’ll go back if this makes you uncomfortable,” Alfie’s voice said, soft and comforting, “but if not, I’ll stay with you and let you cry in my arms.” 

Cas took a moment to process what Alfie has said before he turned around and buried his face in the boy’s chest, shoulders shaking with held back sobs. Alfie just held him tighter, not saying anything. Just letting Cas cry himself to sleep. 

**Notes for the Chapter:**

> Thank you everyone for your kind comments on the last chapter. I still haven't decided whether or not to make the new version ABO or not, but I think I'm leaning towards making it ABO.


	18. Chapter 18

**Notes for the Chapter:**

> I’m so sorry guys, I meant to get this up sooner I just got busy with things and my SPN Dystopia fic proved to be much harder than I thought because I just lost motivation and passion for it right at the end… So it turned out kinda 'blah'. And it was so draining to try and force myself to finish it when I didn't have any ideas on how to go forward with it, so after I was done and had it posted I took a much needed break from all things writing. Which, only lasted less than a week before I was writing again (not writing great, unfortunately, so this chapter may get kinda ugly towards the end. Just a warning.)
> 
> Anyway! Just one more chapter after this and then an epilogue! 
> 
> (And just a P.S.: there’s on sentence in here that has a question mark halfway through and then the sentence just keeps going, and that’s because I recently took a class about grammar and sentence structure and all that good stuff and learned that that’s something you can do and it doesn’t just have to be in poetry or old timey literature! You can put a question mark right in the middle of a sentence if there’s a question in the sentence. And I just wanted to tell you so y’all don’t think I’m illiterate, because there are quite a lot of grammatical errors in this fic, but that’s not one of them, lol.) 
> 
> Also, I talk about Don Quixote in this chapter, but I have never personally read the book, so take what I write about it with a grain of salt. 
> 
> Enjoy! This does happen to be another short chapter, but I hope it’ll tide you over until the next one. Which, should definitely be longer. 
> 
> Vocab You’ll Need For This Chapter:  
> Bobolyne - a fool.  
> Yaldson - literally means “the son of a prostitute.”  
> “Break horizon” - something I made up (I think? maybe?) to basically mean get over the horizon for where you want to go. (I hope that makes sense?)  
> Forecastle deck - the deck at the very front (or bow) of the boat (pronounced: fo'c's'le)

_ March 31, 1696 _

 

Cas could hear everything that was being planned for his and Meg’s wedding. A woman named Ruby sat at the table talking with them, as well. Crowley said she was a marriage ceremony coordinator, and all she did was ask questions. She’d been asking countless questions since everyone sat down and there didn’t seem to be an end in sight. 

“Formal or informal?” Ruby asked. 

“Formal, of course,” Crowley said, taking a big gulp of wine. 

“Big or small?” 

“Big,” Crowley drawled, “Invite everyone in the Kingdom!”

“Well, there’s the guest list,” Ruby said, smiling as she checked off a few things on the parchment she had. “Budget?”

Crowley guffawed at that. “There is no budget! Only the best for my daughter! Even if it is for a second time,” he said, giving Meg a big, creepy grin. 

“Wedding date and place?” Ruby asked, pursing her lips for a moment before looking up at Crowley. “I suppose you’ll want to hold the ceremony at the chapel? The one on the Circle?” 

Michael raised his hand and cleared his throat to gain Meg and Crowley’s attention. 

“The Circle?” He asked, his voice wavering only enough for Cas to notice it. 

Meg groaned and Cas saw her roll her eyes in an exaggerated way. “The small island in the cove. You know? The one over the bridge?”

“Meg,” Crowley chastised, earning another eye roll from Meg. 

“Excuse me, I’m sorry. I had no idea,” Michael said, “I’ve only ever been as far as the castle.” 

“Well, you know now,” Ruby said, just a slight sneer to her voice. “Anyway, when would you like to have the wedding commence? I suppose you’ll want another summer wedding?” 

Crowley smiled at Ruby, something twinkled in his eyes as he nodded his head. 

“July twenty-first?” Ruby said, looking down at her documents as a blush rose to her cheeks. “I see no one has asked for the Circle that day and all of my usual staff and vendors are available.” 

“Perfect,” Meg said, reaching to her plate to swirl her finger in the leftover white sauce from the evening meal that had been served. She brought it up to her mouth as she looked directly at Cas and licked away the cream suggestively. “What do you think, Castiel?” She asked, reaching back down to wipe up some more sauce. 

Cas watched her do it again, only blinking once before he turned back to stare out a window. 

“Whatever you would like, Your Royal Highness,” he said. Meg smiled as Crowley barked out an amused laugh. 

“Already submissive,” Crowley said under his breath so only Meg and Cas had been able to hear. Meg smiled at her father and nodded her head. 

“July twenty-first is the date, then?” Ruby asked after a small silence at the table. 

“Absolutely!” Crowley announced loudly. Ruby looked up to give him a smile.

“Next year, I would think, Your Majesty? There is not enough time to plan a wedding for it to be this year,” she said. Crowley gave her a proud smile. 

“You know me almost as well as I know myself, love,” he said. “Next year, yes.” 

“Would you like Father Tom to officiate again?” 

“Naturally,” Crowley said, taking another large gulp of wine. 

“Perfect,” Ruby said, scribbling something into her documents. She took a long while before looking back up at Crowley. “We’ve gotten a lot done tonight, I need to work out all these details before we can move forward so what do you say we continue this in two months after I’m done? That way I can make certain the vendors will be able to commit to working with me.” 

Crowley leered at Ruby for a moment before looking to Meg to voice their answer. 

“Sounds good to me,” Meg said, darting her eyes to Cas again as Ruby gathered her documents and began making her way out of the hall. When she passed by Crowley’s chair, he grabbed her wrist and pulled her down to whisper something in her ear. Cas heard her giggle softly and gasp. 

“Of course, Your Majesty,” She said quietly. “I’ll be waiting for you in your chambers.” 

Crowley made a growling noise and Ruby giggled again before making her way to the exit. Meg groaned and fixed Crowley with a tired look. 

“Really, father?” She asked him, not even bothering to be quiet about it. “Another one?” 

Crowley only laughed, raising his wine glass in Meg’s direction before downing the rest of it and then calling for more. Meg scoffed, again, and rolled her eyes. Again. She took a moment to stretch out before turning to look at Michael. 

“So… Michael…” she started, “Why, again, were you not able to meet with us all those years ago when we first reached out to you about a marriage proposal?” 

Michael paused, darting his eyes to Cas before he cleared his throat and answered. 

“My son got caught up at the library and ended up losing track of time,” He said. “He came home close to noon, about an hour after your representative left.” 

“So he likes to read?” Crowley asked, turning to look at Cas. “What do you like to read?” 

“Everything,” Cas answered quietly, not looking away from his window. “I like everything.” 

“Sure,” Crowley agreed. “What’s your favorite?” 

“ _ Don Quixote, _ ” Cas said immediately. 

“Isn’t that that Spanish book?” he asked. “The one about the man who goes crazy and sets out on a quest to ‘right all wrongs’ and restore chivalry?” 

Cas nodded, finally turning to face Crowley. He didn’t think the King would occupy his time reading books such as  _ Don Quixote _ . Maybe he wasn’t as bad as people said after all. 

“Yes, that’s the one,” Cas said. 

Crowley’s face soured and he swirled his newly replenished wine. “I tried reading that book,” he said, “but I couldn’t finish it.” 

“Really?” Cas asked, furrowing his brows.  

Crowley nodded uninterestedly. “It was a piece of junk, if you ask me. A man nearing the age of fifty goes out to restore chivalry? Not likely.”

Cas frowned deeply and looked down at the food on his plate. He’d only taken a few bites. 

“There are rumors that that was based on a true story about a man who lived several decades ago.” 

“Yes, Your Majesty. There are such rumors,” Cas whispered, studying his food. 

“They’re not true, you know. Just hopeless wishes of men who want to be more than they are,” Crowley said, waving his hand in the air. “ Alonso Quixano isn’t a great man, either. Took advantage of Sancho Panza. He’s a bobolyne if there ever was one…” 

Cas closed his eyes and blocked out the rest of what Crowley kept on saying about  _ Don Quixote _ . He thought of eating more, but he felt his stomach squeeze at the thought of it, so he clasped his hands together instead, waiting for Crowley’s voice to cease so he could speak. 

“...a nd quite frankly, I’m not convinced he wasn’t a yaldson, either.” 

“Okay, father,” Meg groaned. Cas heard a silence and took his chance. 

“Your Majesty.” He nodded to Crowley. “Your Royal Highness.” A nod to Meg. “Father.” He gave a final nod to Michael and stood up. “Pardon me, but I’m exhausted. I’m going to take my leave and turn in for the night. Thank you for the lovely dinner and excellent wine. It was all very delicious,” Cas said, turning to nod at Alfie in a silent asking for him to follow. He got a quick, almost imperceptible, nod in return. 

Cas and Alfie made a quick exit, not giving anyone time to contradict his wishes. He really was quite tired. He’d found that most of his days were spent in an exhausted haze. The only saving grace was Alfie. 

Alfie had been Cas’s rock through everything. In the two months he’d been in Heaven, he’d done little that he could remember. What he did remember? was of Alfie, holding him or laying on the other side of his bed at night because sometimes it was hard to be held or even touched; but Cas needed the company. It was hard to be alone at night. 

Tonight was no different, and after Alfie had come back from changing into his own nightclothes, he settled under the heavy linens on Cas’s bed and opened his arms in offering. Cas gave it a moment's thought before moving over and settling into Alfie’s arms, snaking his own around Alfie’s waist as he got comfortable. 

“You know,” Alfie started, “I think the King was quite rude about  _ Don Quixote _ . You told him it was your favorite book, and he still said those awful things.”

Cas shrugged. “It’s not a big deal. It’s just his opinion.” He lifted his head to look at Alfie. “I’m not upset by it,” he said, “If that’s what you’re saying.” 

“Oh, good.” Alfie nodded. 

Cas shrugged again, resting his head back on his pillow. “If I’m being honest, I tuned him out after he called Quixano a bobolyne.” 

“Who even uses that kind of language, either?” Alfie scoffed. “‘Bobolyne’? That’s the first time I’ve even heard someone use that word.” 

“Me too,” Cas agreed. Alfie put his chin on the top of Cas’s head and gave him a squeeze.

He lowered his voice and started moving his thumb in slow circles on Cas’s shoulder blade. “How was today, Cas?” Alfie asked seriously. 

“Same as usual.” 

“You didn’t seem as present as usual,” Alfie explained. “Did anything I should know about change?” 

Cas shook his head. “Not really,” he said. “Just… Missing more than usual, I guess.” 

“Tomorrow is a free day, so we can stay in here as long as you want,” Alfie said. Cas hummed to let Alfie know he heard. “Or we could go to the garden? I know you like to smell the flowers and watch the bees. I saw you smile last time.” 

“I do,” Cas whispered. “And I did.” 

“So why don’t we do that?” Alfie sounded hopeful. Cas generally didn’t want to do anything, but he didn’t want to let Alfie down, so he found himself doing a lot of different things with Alfie and going through the motions. From what he could remember of it all, it was all, not surprisingly, tiring. 

Cas stayed silent for a moment, unable to give an actual answer yet because a lump had formed in the back of his throat. He only smiled because he’d been looking at some gardenias and had a flashback to when he’d given Dean a bouquet of asters and gardenias before he left one instance a few years ago. When he came back, Dean still had the flowers. Pressed and tied together and hung up along the headboard of their bed. It had made Cas’s entire week to know that Dean cherished his gifts so much to save them for so long. 

Of course, after he’d come back to the present, he had to stop himself from crying in the middle of the King’s garden. Dean had still had the flowers the last time Cas had been on his ship, but by now, Dean had probably gotten rid of them. 

“Okay,” Cas heard himself answer. “Tomorrow we’ll go to the garden.”

“Great,” Alfie said. “Maybe I’ll see you smile again.” 

Cas nodded his head, although, he sincerely doubted that. 

 

~~~

 

_ April 28, 1696 _

 

Last month, Dean had been sent proof Lisa and Ben were all set up in Heaven at the best Inn—the one the high class people stayed at. Lisa had enough gold to last a year, if not more with how frugal she was. Dean was confident that he could get to Abbadon swiftly and neutralize her, but just in case, he wanted them to be okay unless it took longer than he thought it would. The small envelope containing a piece of his own stationary with Lisa’s handwriting saying,  _ ‘Poughkeepsie’ _ was a godsend. It put his nerves at ease and made it easier to sleep at night. 

Now all that kept him up till twelve in the morning was thoughts of Cas. He felt increasingly guilty about not taking him with and finding somewhere for him to stay until it was safe to come get him again, but he couldn’t risk it. Bobby’s house wasn’t an option because if Abbadon was as smart and connected as Dean though she was—and she was—Bobby would already be found out. Dean’s intuition was proven correct because once they got to Bobby’s place, they found it in ruins. Bobby was either dead, being held hostage, or he’d escaped to some uncharted safe place. Knowing the old man, the third option was the most believable. 

None of the other safe places were viable options to leave Cas because only Bobby knew where they were and now that Abbadon had been to visit him, there was a major chance she had the map of where each house was, and if the positions were reversed, Dean would have a team staked out at each place in case Abbadon or Abbadon’s loyalists showed up. 

Even if she didn’t have the map, Dean would rather be safe than sorry. 

And King Crowley was not a man to rush into things, anyway, so, as long as Dean got done with Abbadon in a timely manner, Cas wouldn’t have to worry about marriage or Meg or Michael or anything ever again. 

That line of thought helped him sleep, but it didn’t mean it got rid of his guilt. He often woke up after only four hours of sleep and couldn’t get back to bed no matter how hard he tried. Which meant he was up and ready by the time anyone came to wake him. 

Today already appeared to be different, though. It was two in the morning and Dean still couldn’t sleep. He could feel his guilt for leaving Cas behind squeezing itself tighter and tighter around his lungs with each breath and the longer he thought about what he’d done, the worse it got. 

“Dean!” Sam’s muffled voice came through his door. Dean let out a breath he didn’t know he’d been holding and got up to answer. He was met with a grim looking Sam followed by a pale Chuck. 

“What’s the matter?” Dean asked, looking from Sam to Chuck and back again. 

“We’re almost to Lawrence,” Chuck said, his voice quivering just enough to be noticeable. “But… There’s a problem.” 

Dean raised an eyebrow in response and to prompt them to tell him the problem. Neither of the two answered at first, though. Instead, they shared a glance before Sam nodded to Chuck and he went scurrying away. 

“We saw Abbadon’s ship,” Sam said. Dean nodded his head, getting impatient waiting for the other shoe to drop. “She’s not alone,” Sam finished. Now, even his voice wavered and for Sam to be shaken enough to show it? That meant something truly tremendous had to be waiting for Dean. 

“How many others are there?” Dean asked, taking a step forward. Sam stepped out of his way and let Dean walk out to the deck, following close behind. 

“I don’t know,” he said, “We can only see seven other ships, but there’s no telling just how many more there will be once we break horizon.” 

“There’s seven?” Dean repeated, picking up his pace and making a beeline for the forecastle deck. Chuck was up in the crow’s nest doing what he did best. Several other sailors were up along the main mast, waiting for any more news on how many ships were at Lawrence. 

“They’re not well known crews,” Sam said in effort to make the situation seem better. “The, uh, it looks like the Demon Raiders, Ghost Bandits of the Void, Black Swords, Hounds of the South, and.... More smaller ships that don’t have flags I can make out or see.” 

“So, we’re up against a whole armada,” Dean said, more to himself than to anyone else. 

“And we don’t know how many more ships there really are,” Sam said quietly. Dean reached into his pocket to pull out his spyglass, quickly lifting it to his eye. He saw the ships Sam had mentioned, plus a few more now. 

“There’s more over the horizon,” Dean said. “I can see the main mast of some of them.” 

“Chuck will keep us informed, too,” Sam said, stepping closer to Dean and putting a hand on his shoulder. “If there are too many more, though, Dean… I don’t know what we’re going to do. We only have so much man power and there are some pretty substantial ships out there. I don’t know if—” 

“We’ll find a way,” Dean interrupted, snapping his spyglass closed and stuffing it into his pocket. “We always find a way, Sam. This time is no different.” 

“But—” 

“Trust me,” Dean interrupted again, “Sam, please. I have faith in our odds, but I can’t do this if you don’t trust me as your captain.” 

Sam’s face became all hard lines and he gave Dean a affirming nod. 

“I trust you,” he said. Dean patted his shoulder in thanks. 

“Call everyone to the main deck for me, please,” he said. “I need to let them know what’s going on.” 

Sam said something to let him know he heard and then was off, yelling for people to gather on the main deck. As Sam spread the news, Dean stood still, going over everything in his head. 

The cannons were as ready as they could be, but they hadn’t been tested. Now was as good a time as any, he supposed. He just prayed to luck that they would work, or else they would be blown out of the water faster than he could get letters to other crews he was friendly with asking for help. On the other hand, if the cannons worked, they could hold their ground until help arrived, if it arrived. If it didn’t, it would be hard, but Dean was confident in his crews ability to fight. 

Next was a battle plan and they had plenty to choose from. Kevin and Ash would be able to help there. After that, all that was left was how many hands on deck they’d have; because before every battle Dean always gave his crew the option to abandon ship. To go home to their families or wherever they called home. If there were any weak links in the chain, they’d loose anchor and never be able to right themselves. If there was even one person who wasn’t dedicated to the battle, that meant there was a chance they could miscalculate. 

Drastic, Dean knew, but he wouldn’t let it be any other way. 

“Dean!” Sam came bounding up the stairs to Dean with Charlie, Jo, Gilda, Benny, and the rest of his officers behind him. “Everyone’s ready,” Sam said. Dean nodded, looking from Sam to the rest of his officers. 

“As always, you have the option to abandon now. I won’t—”

“Fuck, Dean,” Jo said, exasperated. 

“Spare us the usual spiel,” Kevin said. 

“We’re not leaving,” Charlie said. Dean looked at all of them and gave each one an appreciative smile before heading over to the edge of the forecastle deck and addressing the rest of his crew. 

“I’m going to be honest with you all,” he started, “we’re not sure how vast of an army is waiting for us once we reach Lawrence. So far we can see eight major crews, and we haven’t broken horizon yet, so we’re very much in the blind with how many ships we’ll have to take down.” A small hush went through the sailors and Dean let it die down before continuing. “As per usual, before we go into a major battle I give every sailor the option to leave. To go home and not have anything held against them. I ask that anyone who wishes to go, go now because once we start fighting, if you abandon ship… When we win you’ll be on our list.” 

Dean finished with a look around at everyone on the main deck, taking in all the different expressions. About a third looked worried and Dean was certain they were going to abandon ship. That would lower their chances of survival even more, and that itself made Dean begin preparations on how to get more gold to Lisa and word to Cas about his imminent death. 

“None of us are leaving!” Someone yelled, drawing everyone’s attention to him. Dean recognized him at Victor. Victor Henriksen, one of Dean’s oldest and most loyal mates. He’d been with Dean almost since the beginning. “We’re not abandoning.” 

There were shouts of agreement all around. Even from the ones that still wore worry lines on their faces nodded their heads. 

“We’re not abandoning you,” Victor yelled again, looking around at everyone. Dean looked out at everyone again, nodding and agreeing. “We’re fighting  _ for _ you!” 

“For Winchester!” Someone else screamed out, earning the crowds approval in the form of a battle cry. Dean felt his chest swell with pride and admiration for his crew.  _ Winchester _ didn’t mean just Dean anymore. Not to Dean, at least.  _ Winchester  _ meant everyone on this ship and if they were going to fight for him, he would fight for them, too. 

Dean raised his blade to the sky, smiling as the rest of his crew did the same. “For Winchester!” 


	19. Chapter 19

**Notes for the Chapter:**

> So sorry this took so long. I got writers block and it took me forever to push through it, and I'm even still not sure if I'm completely out of it. I'm not sure how well I wrote it because of writers block... Either way, though, I hope this doesn't suck.
> 
> So, one more chapter after this one and then an epilogue! Should be coming soon unless writers block decides to flare up again. :P

_July 21, 1696_

 

As time went on in the Kingdom, the more the plans came together for the wedding. Crowley and Ruby never checked in with Castiel or Michael about what they thought, they focused only on what Meg wanted or thought about any small detail.

 _‘Meg, what flowers do you want? I think we should try to stay away from the traditional roses or tulip or any kind of lily_.’

_‘Meg, how do you want to arrive at the chapel? Carriage or on horseback? What about when you and Castiel leave?’_

_‘Meg, where do you want to hold the rehearsal dinner?’_

_‘Meg, do you want to look over some sketches I’ve made for the cake? Or if you trust me enough, I can do something grand and surprise you?’_

_‘Meg, what do you want on the menu?’_

Et cetera, et cetera, et cetera. It was like Cas was invisible. Not that he cared much. Meg and Crowley could throw whatever kind of wedding they wanted and Cas wouldn’t care.

It was because of his apathy towards the wedding, and his future, really, that Alfie had finally broke and took things into his own hands.

One day when Crowley had said there would be no planning—for one reason or another, Cas had immediately departed for his chambers and simply crawled back into bed. Alfie tried to talk him out of bed, but when he got nothing, he finally just dragged Cas out and sat him down. He slapped a slab of wood into his lap, a paintbrush in his hand and told Cas to paint what he felt. Cas went through the motions first, just to make Alfie happy, but he found that not only was he good at it, he found that he _liked_ it. How it made him feel when he was painting and how a weight seemed to lift from his shoulders when he finished.

Cas had painted several pieces and each time he finished one, he felt better. Like his entire future hadn’t just collapsed. Instead of the numbness he had been constantly feeling since Dean, there was a sense of relief. And that feeling of relief gave way to other feelings. It allowed him to feel angry at Dean and betrayed by him. But it also brought back the love he had for him. In turn, that love made his sliver of hope grow again.

The conflicting emotions sometimes made him want to shut down again, but those were the times when he was painting he turned to Alfie for help. He didn’t want to spend the rest of his life going through the motions, exhausted by even the littlest of things. Cas wanted to survive with at least some comfortability, and if that meant dealing with the complications of feeling, he was fine to do it.

Cas also didn’t want to go through the rest of his life thinking it was empty without Dean. It was empty of certain things like romance and sex, but that didn’t mean Cas’s life was completely empty. He still had Alfie and painting, and a future without his father. He had a life before Dean, so that meant he could have one after Dean.

“Castiel,” Alfie’s voice pulled Cas out of his thoughts. “Uh, well, her Royal Highness, Princess Meg is here to speak with you.”

Cas turned from his seat by his window to look at Alfie and Meg standing at the door to his room.

“Hello, your Royal Highness,” Cas greeted, standing up to give a quick nod of respect. Meg stepped passed Alfie, glaring at him.

“I’ll leave you to it,” Alfie said, glaring in his own way right back at Meg. He made a quick exit, shutting the door softly as Meg came to stand at the foot of Cas’s bed. She looked around for a moment before her gaze stopped at one of the paintings Cas had hung over his bed. It was of the ocean at sunset. An island was on the horizon and had light bursting out from behind it.

Meg’s face contorted into a look of disapproval. “You paint?” She asked, looking to the next painting.

“Yes, Your Highness. I took it up as a hobby,” Cas said weakly.

“Yes,” Meg said in a bored manner. She moved over to Cas’s desk and looked to Cas’s most recent finished painting and studied it. “This is a pirate ship, is it not?”

“It is.”

“Huh.” Meg leaned down to study it more and smirked knowingly. “I’ve seen that flag before.”

“Have you?” Cas began tapping his foot nervously. Those flags were the flags Dean used to signal his status to other pirates in the sea. They had the same sun and pentagram all his mates had to get tattooed on themselves when they joined his crew. It was the Winchester Insignia.

“I have,” Meg said. She looked over to Cas, quirking an eyebrow up. “It’s the flag of Dean _the Righteous Man_ Winchester, isn’t it?”

Cas looked down to his current painting and swirled his brush around to make a petal. “I wouldn’t know. I saw many pirate ships dock in Heaven. Some flags stand out more than others.”

“Or some _man_ stands out more.”

Cas paused. “What do you mean by that?”

“I had a hunch about you. I told father that you were a sodomizer but he didn’t believe me,” Meg said, “but I am right, aren’t I?”

“I… I don’t know what you mean,” Cas said quietly.

“Don’t play coy, I know you know what I mean. You aren’t attracted to women.”

Cas put his brush down. “I’m truly sorry, but I don’t understand what you expect me to say.”

“I heard rumors from a handful of the servants in your house about how whenever Dean Winchester’s ship docked, you acted differently. More lively,” Meg said, stepped up to stand next to Cas. “Now, seeing your painting accompanied to the fact that I’ve been acting suggestively towards you only to gain nothing? I know for fact that you’re excited by men.”

“I can’t confirm your beliefs and I don’t appreciate you...insulting me,” Cas said.

“Can you deny them?”

“Of course, I’m not attracted to men. I’ve never been attracted to—”

“Can you deny you’re not excited by Dean Winchester?” Meg laid her hand down on Cas’s shoulder.

“I… I’m not.”

“Care to prove it?” Meg whispered. Cas froze in his spot as Meg’s hand slid from his shoulder to his chest. “Care to prove you’re excited by me, at the very least,” she continued, her hand sliding lower and lower. Cas could feel his heart pounding in his chest and he wanted nothing more to shrug her off and get as far away as he could… But he was frozen as Meg’s hand stopped just above his waistband. “I wouldn’t mind having some fun, even if we’re not married yet. It’s been so long since my last husband and I laid together. I don’t believe anyone would blame us for jumping the gun a bit. Do you?” Cas held his breath. “What do you say?” Meg whispered, her mouth right by Cas’s ear. Her pinky finger slipped into his waistband and Cas jumped up away from her. His painting fell to the ground, but he didn’t care.

“No, stop,” he blurted out. “No. I don’t want to be with you.”

Meg grinned victoriously. “Just as I thought!”

“No, it’s not,” Cas said firmly.

“Hm.” Meg sat down in Cas’s chair, eyeing him curiously.

“I’m not attracted to women, but I’m not attracted to men either,” Cas explained. Meg raised an eyebrow and pursed her lips. She was quite for a long while, only moving her eyes up and down Cas’s figure. She looked to be contemplating something intense and important. The way she studied him unnerved Cas greatly.

Meg finally sighed and stood up, sauntering away from Cas. “Alright,” she said. “It’s no matter, though. You don’t have to be attracted to me. All I need is for you to be able to give me an heir.” Cas watched as she made her way towards his door. She turned around once she reached it and gave Cas a serious and dark look. “Word of advice, Castiel: find something that arouses you. If you don’t, I’m afraid you’ll end up like my last husband.”

Cas’s breath caught in his throat painfully. “What?”

“Oh, yes, very sad what happened to him. An accident that could’ve been avoided, if only he’d been able to give me an heir. But unfortunately, he found himself at the top of the set of stairs to the dungeon and he…” Meg smiled mischievously. “Tripped.”

Cas felt dizzy as Meg took her exit. He stumbled over to his desk, leaning against it as he heard his door open and someone speak from miles away.

Meg’s last husband… He hadn’t tripped. He’d been pushed. Murdered, because he wasn’t able to impregnate Meg. And the same thing would happen to him when he wouldn’t be able to provide an heir for her either.

“Cas?” Alfie’s hand on his back snapped him out of his daze and Cas was able to notice that someone else was in the room too. “Are you alright? What happened?”

Cas looked past Alfie and saw a face he thought he’d never see again.

“Gabe?” He got out before his throat closed up.

“Hey Cas,” Gabe said. Cas let out a shuddering breath before launching himself at his uncle.

“Gabe,” he cried, “I’m scared.”

Gabe’s arms came around him, hugging him tight and surrounding him in comforting embrace. “I know,” he said, “I know.”

 

~~~

 

_December 16, 1696_

 

“We’ve eliminated the last ship,” Benny said. “We’re safe until we make it to shore. And we should get there by sunset.”

Dean nodded grimly. “How many have we lost?” He asked.

Benny looked away as he answered. “Just over half our people.”

“That doesn’t bode well for us.”

“Nay.”

“But we can’t give up yet, everyone knows that. We’ve reached the shore and defeated Abbadon’s armada.”

“Now we need to get through her army on land.”

“After that, getting to her should be easy,” Dean said, looking down at his boots. “The fleet was her first defense. The second obstacle shouldn’t be so difficult.”

“I agree,” Benny said.

“We can do this,” Dean said, more as an affirmation to himself than anything else.

“I agree with that, too,” Benny said. Dean looked up at him and nodded with some finality.

“Alright. Let’s get out of here and join the rest of the crew,” Dean said. Benny waited for Dean to lead the way, but ended up watching him curiously when he didn’t move.

“You know, I believe you did the right thing.”

Dean looked up at Benny. “What do you mean?”

“Leaving Cas there.” Dean’s jaw clenched, but Benny continued, “We’ve lost over half our people. Cas has no training, not much muscle, he would have been slaughtered. If he hadn’t been killed so far, he would most likely be killed as soon as we set foot on land.”

“He has his Grace.”

“His Grace is meant to heal. Protect him at best, it’s not meant to fight.”

“You don’t—it… He…” Dean hit his fist against the table. “You don’t know that. No one knows that. Maybe I could have found somewhere for him to stay safe. We have allies all over the place, why didn’t I think to leave him with any of them? At least then he wouldn’t have had to stay in Heaven and have a wedding looming over his head. If I hadn’t—”

“Dean— _Captain,_ you need to focus on what’s important right now,” Benny said, “You’re looking for reasons to blame yourself, and we have a full blown war waiting for us outside this cabin. We have to win.”

Dean straightened up. “I’m sorry. You’re right.”

“Good.” Benny stared at Dean for a short moment. “You alright, then?”

Dean looked into Benny’s eyes and nodded. He picked up his blades and sheathed then in his belt. “Let’s go,” He said and exited his cabin. Benny followed closely, watching as with each step Dean transformed into the tactical and formidable Captain he knew Dean to be. “When we get onto the ground we need to be fast.”

“Aye.”

“It may even be worthwhile to wait at least a day before we disembark,” Dean continued. “Make as many come to us as we can.”

“Aye.”

“It would confuse them, at the very least. And we need every advantage we can get.”

“Aye.”

“Before we do anything we need to send a scout team to shore. Charlie, Sam, and Garth will go. They’re a good team. Effective.”

“Aye, Captain.”

“Our best soldiers will be placed depending on what they report back.”

“Aye.”

“And we need to be ruthless. We need to be absolutely—”

“Captain!”

Both Dean and Benny looked to who called them. Chuck was standing towards the stern, holding a spyglass with shaky hands. Dean and Benny joined him, pulling out their own spy glasses and looking through them in the direction Chuck had his pointing.

Dean saw ships. Lots of them.

“More are coming our way,” Chuck said, voice shaking almost as much as his hands were.

“I can see nine so far, but there are more coming in from behind them,” Benny said quietly.

“Oh god,” Chuck said. “Do you think it’s reinforcements for Abbadon?”

Benny sighed. “Maybe. Dean?”

Dean dropped his spyglass slowly, taking all the new information in. He wouldn’t show it, but he felt just as Chuck did. It was more likely than anything that those ships coming were going to obliterate them. Abbadon had thought of everything. She came prepared. Dean figured he should’ve known. He should have seen this coming. It’s what he would have done.

“Dean!” Chuck yelled in surprise. “They’re raising their flags!”

Dean pulled his spyglass back up to his eye and froze.

“Dean…” Benny said, a kind of awe in his voice. “Those aren’t Abbadon’s flags.”

“Those are—”

“Those are our flags,” Dean interrupted. “Those reinforcements are here to fight with us.”


End file.
